HCID 70403466, compound → HCID 57269490, compound

HRID 1252523Notes

Reaction equation

HRID 1252523 reaction equation
C(OC([NH:11][C@@H:12]([CH2:37][C:38](=[O:57])[NH:39][CH:40]([C:49]1[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=1)[C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=1)[C:13]([NH:15][C@@H:16]([C@H:20]([NH:22][C@H:23]([C:34]([OH:36])=[O:35])[CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)[CH3:21])[C:17]([OH:19])=[O:18])=[O:14])=O)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[NH2:11][C@@H:12]([CH2:37][C:38](=[O:57])[NH:39][CH:40]([C:49]1[CH:50]=[CH:51][C:52]([O:55][CH3:56])=[CH:53][CH:54]=1)[C:41]1[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=1)[C:13]([NH:15][C@@H:16]([C@H:20]([NH:22][C@H:23]([C:34]([OH:36])=[O:35])[CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)[CH3:21])[C:17]([OH:19])=[O:18])=[O:14]

Participants

4

Reactant 1

HCID 70403466HCID 70403466, compound

Product 1

HCID 57269490HCID 57269490, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of (2S,3R)-2-[[(2S)-2-benzyloxycarbonylamino-3-[N-[bis(4-methoxyphenyl)methyl]carbamoyl]propionyl]amino]-3-[[(1S)-1-carboxy-2-(3-indolyl)ethyl]amino]butyric acid (800 mg) in acetic acid (20 ml) was hydrogenated under medium pressure (3 atm.) for 8 hours at room temperature in the presence of 10% palladium on carbon (120 mg). After removal of the catalyst, the solution was evaporated in vacuo and the residue was solidified with water to give (2S,3R)-2-[[(2S)-2-amino-3-[N-[bis(4-methoxyphenyl)methyl]carbamoyl]propionyl]amino]-3-[[(1S)-1-carboxy-2-(3-indolyl)ethyl]amino]butyric acid (460 mg) as a yellow brown powder.

Workup

  1. customAfter removal of the catalyst
  2. customthe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-75bf3d2ec90c41ec9c6ee14e7db312af
Source dataset
uspto-grants-1988_05
Patent number
US04743614

Reaction notes

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