Benzyl mercaptan → HCID 131736696, compound

HRID 1482270Notes

Reaction equation

HRID 1482270 reaction equation
[CH2:1]([C@@H:8]([C:66](=[O:130])[NH:67][CH2:68][C:69](=[O:129])[N:70]([CH3:128])[C@@H:71]([CH2:124][CH:125]([CH3:127])[CH3:126])[C:72](=[O:123])[N:73]([CH3:122])[C@@H:74]([CH:119]([CH3:121])[CH3:120])[C:75](=[O:118])[NH:76][C@@H:77]([CH2:111][C:112]1[CH:117]=[CH:116][CH:115]=[CH:114][CH:113]=1)[C:78](=[O:110])[NH:79][C@H:80]([C:85](=[O:109])[N:86]([CH3:108])[C@@H:87]([CH2:101][C:102]1[CH:107]=[CH:106][CH:105]=[CH:104][CH:103]=1)[C:88](=[O:100])[NH:89][C@@H:90]([CH3:99])[C:91](=[O:98])[N:92]1[CH2:97][CH2:96][CH2:95][CH2:94][CH2:93]1)[CH2:81][C:82](O)=[O:83])[N:9]([CH3:65])[C:10](=[O:64])[C@H:11]([C@H:42]([O:44][C:45]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH3:43])[NH:12][C:13](=[O:41])[C@H:14]([CH2:37][CH:38]([CH3:40])[CH3:39])[N:15]([CH3:36])[C:16](=[O:35])[C@H:17]([CH:32]([CH3:34])[CH3:33])[NH:18][C:19](=[O:31])[C@H:20]([CH3:30])[N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:131]1([CH2:137][SH:138])[CH:136]=[CH:135][CH:134]=[CH:133][CH:132]=1.CC(C)N=C=NC(C)C>ClCCl.CN(C=O)C.CN(C)C1C=CN=CC=1>[CH2:1]([C@@H:8]([C:66](=[O:130])[NH:67][CH2:68][C:69](=[O:129])[N:70]([CH3:128])[C@@H:71]([CH2:124][CH:125]([CH3:127])[CH3:126])[C:72](=[O:123])[N:73]([CH3:122])[C@@H:74]([CH:119]([CH3:121])[CH3:120])[C:75](=[O:118])[NH:76][C@@H:77]([CH2:111][C:112]1[CH:117]=[CH:116][CH:115]=[CH:114][CH:113]=1)[C:78](=[O:110])[NH:79][C@H:80]([C:85](=[O:109])[N:86]([CH3:108])[C@@H:87]([CH2:101][C:102]1[CH:103]=[CH:104][CH:105]=[CH:106][CH:107]=1)[C:88](=[O:100])[NH:89][C@@H:90]([CH3:99])[C:91](=[O:98])[N:92]1[CH2:97][CH2:96][CH2:95][CH2:94][CH2:93]1)[CH2:81][C:82](=[O:83])[S:138][CH2:137][C:131]1[CH:136]=[CH:135][CH:134]=[CH:133][CH:132]=1)[N:9]([CH3:65])[C:10](=[O:64])[C@H:11]([C@H:42]([O:44][C:45]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[CH3:43])[NH:12][C:13](=[O:41])[C@H:14]([CH2:37][CH:38]([CH3:40])[CH3:39])[N:15]([CH3:36])[C:16](=[O:35])[C@H:17]([CH:32]([CH3:34])[CH3:33])[NH:18][C:19](=[O:31])[C@H:20]([CH3:30])[N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 7509Benzyl mercaptanHCID 12734DiisopropylcarbodiimideHCID 117736126HCID 117736126, compound

Product 1

HCID 131736696HCID 131736696, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(6S,9S,12S,15S,18S,24S,27S,30S,33S)-18,30-dibenzyl-12,24-diisobutyl-9,27-diisopropyl-2,2,5,6,11,17,23,26-octamethyl-33-(methyl((S)-1-oxo-1-(((S)-1-oxo-1-(piperidin-1-yl)propan-2-yl)amino)-3-phenylpropan-2-yl)carbamoyl)-4,7,10,13,16,19,22,25,28,31-decaoxo-15-((R)-1-(trityloxy)ethyl)-3-oxa-5,8,11,14,17,20,23,26,29,32-decaazapentatriacontan-35-oic acid (Compound SP-518) (50.0 mg, 0.028 mmol) was dissolved in dichloromethane (320 μl) and DMF (80 μl), phenylmethanethiol (6.93 mg, 0.056 mmol), DIC (7.04 mg, 0.056 mmol) and N,N-dimethylpyridin-4-amine (2.58 mg, 0.021 mmol) were added and the mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by column chromatography (10 mM aqueous ammonium acetate solution:methanol) to afford the title compound (SP-520) (37.6 mg, 71.0%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe resulting residue was purified by column chromatography (10 mM aqueous ammonium acetate solution:methanol)

Sources & evidence

ORD record
ord-7b805363e4ed4ef39707591c1a51e1da
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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