Benzyl mercaptan → HCID 131736692, compound

HRID 1482255Notes

Reaction equation

HRID 1482255 reaction equation
[NH2:1][C:2](=[O:93])[CH2:3][NH:4][C:5](=[O:92])[C@@H:6]([NH:13][C:14](=[O:91])[C@@H:15]([N:17]([CH3:90])[C:18]([C@H:20]([CH2:86][C:87](O)=[O:88])[NH:21][C:22](=[O:85])[C@H:23]([CH2:78][C:79]1[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1)[NH:24][C:25](=[O:77])[C@H:26]([CH:74]([CH3:76])[CH3:75])[NH:27][C:28](=[O:73])[C@H:29]([CH3:72])[NH:30][C:31](=[O:71])[C@H:32]([CH2:67][CH:68]([CH3:70])[CH3:69])[N:33]([CH3:66])[C:34](=[O:65])[CH2:35][NH:36][C:37](=[O:64])[C@H:38]([CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[N:39]([CH3:56])[C:40](=[O:55])[C@H:41]([CH3:54])[NH:42][C:43](=[O:53])[CH2:44][NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:19])[CH3:16])[CH2:7][O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[C:94]1([CH2:100][SH:101])[CH:99]=[CH:98][CH:97]=[CH:96][CH:95]=1.CC(C)N=C=NC(C)C>ClCCl.CN(C=O)C.CN(C)C1C=CN=CC=1>[NH2:1][C:2](=[O:93])[CH2:3][NH:4][C:5](=[O:92])[C@@H:6]([NH:13][C:14](=[O:91])[C@@H:15]([N:17]([CH3:90])[C:18]([C@H:20]([CH2:86][C:87](=[O:88])[S:101][CH2:100][C:94]1[CH:99]=[CH:98][CH:97]=[CH:96][CH:95]=1)[NH:21][C:22](=[O:85])[C@H:23]([CH2:78][C:79]1[CH:80]=[CH:81][CH:82]=[CH:83][CH:84]=1)[NH:24][C:25](=[O:77])[C@H:26]([CH:74]([CH3:75])[CH3:76])[NH:27][C:28](=[O:73])[C@H:29]([CH3:72])[NH:30][C:31](=[O:71])[C@H:32]([CH2:67][CH:68]([CH3:69])[CH3:70])[N:33]([CH3:66])[C:34](=[O:65])[CH2:35][NH:36][C:37](=[O:64])[C@H:38]([CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[N:39]([CH3:56])[C:40](=[O:55])[C@H:41]([CH3:54])[NH:42][C:43](=[O:53])[CH2:44][NH:45][C:46](=[O:52])[O:47][C:48]([CH3:50])([CH3:51])[CH3:49])=[O:19])[CH3:16])[CH2:7][O:8][C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

7

Reactant 3

HCID 7509Benzyl mercaptanHCID 12734DiisopropylcarbodiimideHCID 117736099HCID 117736099, compound2×

Product 1

HCID 131736692HCID 131736692, compoundYield 21.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(9S,12S,18S,21S,24S,27S,30S)-30-(((S)-1-(((S)-1-((2-Amino-2-oxoethyl)amino)-3-(tert-butoxy)-1-oxopropan-2-yl)amino)-1-oxopropan-2-yl)(methyl)carbamoyl)-12,27-dibenzyl-18-isobutyl-24-isopropyl-2,2,9,11,17,21-hexamethyl-4,7,10,13,16,19,22,25,28-nonaoxo-3-oxa-5,8,11,14,17,20,23,26,29-nonaazadotriacontan-32-oic acid (Compound P-145, (Boc-Gly-Ala-MePhe-Gly-MeLeu-Ala-Val-Phe-Asp-MeAla-Ser(tBu)-Gly-NH2)) (50.0 mg, 0.038 mmol) was dissolved in dichloromethane (320 μL) and DMF (80 μL), phenylmethanethiol (9.49 mg, 0.076 mmol), DIC (9.64 mg, 0.076 mmol) and N,N-dimethylpyridin-4-amine (3.54 mg, 0.029 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 (11.8 mg, 21.8%).

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-b52b643d0d03457aba01dada3197f3fa
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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