HCID 131710187, compound → HCID 131710186, compound

HRID 1606842Notes

Reaction equation

HRID 1606842 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:11]([NH:13][C@H:14]([C:24]([NH:26][C@H:27]([C:30]([NH:32][C@H:33]([C:35]([NH:37][C@H:38]([C:48]([NH:50][C@H:51]([C:53]([NH:55][C@H:56]([C:64]([N:66]1[CH2:109][CH2:108][CH2:107][C@H:67]1[C:68]([NH:70][C@H:71]([C:76]([NH:78][C@H:79]([C:89]([NH:91][C@H:92]([C:100]([O:102][C:103]([CH3:106])([CH3:105])[CH3:104])=[O:101])[CH2:93][C:94]1[CH:99]=[CH:98][CH:97]=[CH:96][CH:95]=1)=[O:90])[CH2:80][CH2:81][C:82](=[O:88])[O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:77])[CH2:72][CH:73]([CH3:75])[CH3:74])=[O:69])=[O:65])[CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)=[O:54])[CH3:52])=[O:49])[CH2:39][CH2:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:36])[CH3:34])=[O:31])[CH2:28][OH:29])=[O:25])[CH2:15][CH2:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7]>[Pd].C(O)(=O)C>[NH2:1][C@H:2]([C:11]([NH:13][C@H:14]([C:24]([NH:26][C@H:27]([C:30]([NH:32][C@H:33]([C:35]([NH:37][C@H:38]([C:48]([NH:50][C@H:51]([C:53]([NH:55][C@H:56]([C:64]([N:66]1[CH2:109][CH2:108][CH2:107][C@H:67]1[C:68]([NH:70][C@H:71]([C:76]([NH:78][C@H:79]([C:89]([NH:91][C@H:92]([C:100]([O:102][C:103]([CH3:104])([CH3:106])[CH3:105])=[O:101])[CH2:93][C:94]1[CH:95]=[CH:96][CH:97]=[CH:98][CH:99]=1)=[O:90])[CH2:80][CH2:81][C:82](=[O:88])[O:83][C:84]([CH3:85])([CH3:86])[CH3:87])=[O:77])[CH2:72][CH:73]([CH3:75])[CH3:74])=[O:69])=[O:65])[CH2:57][C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1)=[O:54])[CH3:52])=[O:49])[CH2:39][CH2:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:36])[CH3:34])=[O:31])[CH2:28][OH:29])=[O:25])[CH2:15][CH2:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

4

Reactant 1

HCID 131710187HCID 131710187, compound

Product 1

HCID 131710186HCID 131710186, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

67.25 g. (42.15 mmoles) of Z-29-39-OtBu are dissolved in 1300 ml. of 80 % acetic acid, and the mixture is hydrogenated in the presence of palladium-on-carbon. At the end of the reaction the catalyst is filtered off, and the filtrate is evaporated to dryness. The residue is triturated with ether, the solid is filtered off, and dried. 63.8 g. (95%) of H-29-39OtBu are obtained. M.p.: 128°-132° C (under decomposition), Rf5 = 0.3.

Workup

  1. customAt the end of the reaction the catalyst
  2. filtrationis filtered off
  3. customthe filtrate is evaporated to dryness
  4. customThe residue is triturated with ether
  5. filtrationthe solid is filtered off
  6. customdried
  7. custom(95%) of H-29-39OtBu are obtained

Sources & evidence

ORD record
ord-5666657c62e24b06b27528a03d03e017
Source dataset
uspto-grants-1976_04
Patent number
US03953415

Reaction notes

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