HCID 131710185, compound → HCID 131710184, compound

HRID 1606841Notes

Reaction equation

HRID 1606841 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:5]([NH:7][C@H:8]([C:10]([NH:12][C@H:13]([C:23]([NH:25][C@H:26]([C:28]([NH:30][C@H:31]([C:39]([N:41]1[CH2:84][CH2:83][CH2:82][C@H:42]1[C:43]([NH:45][C@H:46]([C:51]([NH:53][C@H:54]([C:64]([NH:66][C@H:67]([C:75]([O:77][C:78]([CH3:81])([CH3:80])[CH3:79])=[O:76])[CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)=[O:65])[CH2:55][CH2:56][C:57](=[O:63])[O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:52])[CH2:47][CH:48]([CH3:50])[CH3:49])=[O:44])=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:29])[CH3:27])=[O:24])[CH2:14][CH2:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:11])[CH3:9])=[O:6])[CH2:3][OH:4]>[Pd].C(O)(=O)C>[NH2:1][C@H:2]([C:5]([NH:7][C@H:8]([C:10]([NH:12][C@H:13]([C:23]([NH:25][C@H:26]([C:28]([NH:30][C@H:31]([C:39]([N:41]1[CH2:84][CH2:83][CH2:82][C@H:42]1[C:43]([NH:45][C@H:46]([C:51]([NH:53][C@H:54]([C:64]([NH:66][C@H:67]([C:75]([O:77][C:78]([CH3:79])([CH3:81])[CH3:80])=[O:76])[CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)=[O:65])[CH2:55][CH2:56][C:57](=[O:63])[O:58][C:59]([CH3:60])([CH3:62])[CH3:61])=[O:52])[CH2:47][CH:48]([CH3:50])[CH3:49])=[O:44])=[O:40])[CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:29])[CH3:27])=[O:24])[CH2:14][CH2:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:11])[CH3:9])=[O:6])[CH2:3][OH:4]

Participants

4

Reactant 1

HCID 131710185HCID 131710185, compound

Product 1

HCID 131710184HCID 131710184, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

78.95 g. (60.15 mmoles) of Z-31-39-OtBu are dissolved in 1500 ml. of 80 % acetic acid, and the mixture is hydrogenated in the presence of palladium-on-carbon. When the reaction terminates, the catalyst is filtered off, and the filtrate is evaporated to dryness. The residue is triturated with ether and filtered. 74.35 g. (99 %) of H-31-39-OtBu are obtained. M.p.: 105°C (under decomposition), Rf7 = 0.5.

Workup

  1. customWhen the reaction terminates
  2. filtrationthe catalyst is filtered off
  3. customthe filtrate is evaporated to dryness
  4. customThe residue is triturated with ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-e6fb8dbde80f4aa8866b232e1bf7c902
Source dataset
uspto-grants-1976_04
Patent number
US03953415

Reaction notes

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