HCID 22942118, compound → HCID 22942119, compound

HRID 362149Notes

Reaction equation

HRID 362149 reaction equation
C([O:8][C:9](=[O:74])[C@H:10]([CH2:68][CH:69]1[CH2:73][CH2:72][CH2:71][CH2:70]1)[NH:11][C:12](=[O:67])[C@H:13]([C:63]([CH3:66])([CH3:65])[CH3:64])[NH:14][C:15](=[O:62])[C@H:16]([CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[CH3:61])[NH:17][C:18](=[O:53])[C@H:19]([CH2:44][CH2:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49])[NH:20][C:21](=[O:43])[C@H:22]([CH2:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[NH:23][C:24](=[O:34])[CH2:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])C1C=CC=CC=1>[Pd]>[C:30]([O:29][C:27]([CH2:26][CH2:25][C:24]([NH:23][C@H:22]([C:21]([NH:20][C@H:19]([C:18]([NH:17][C@H:16]([C:15]([NH:14][C@H:13]([C:12]([NH:11][C@H:10]([C:9]([OH:74])=[O:8])[CH2:68][CH:69]1[CH2:73][CH2:72][CH2:71][CH2:70]1)=[O:67])[C:63]([CH3:64])([CH3:65])[CH3:66])=[O:62])[CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[CH3:61])=[O:53])[CH2:44][CH2:45][C:46](=[O:52])[O:47][C:48]([CH3:49])([CH3:51])[CH3:50])=[O:43])[CH2:35][C:36](=[O:42])[O:37][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:34])=[O:28])([CH3:31])([CH3:32])[CH3:33]

Participants

3

Reactant 1

HCID 22942118HCID 22942118, compound

Product 1

HCID 22942119HCID 22942119, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 230 mg (0.223 mmol) of N-[N-[N-[N-[N-[3-(tert-butoxycarbonyl)propionyl]-O-tert-butyl-L-α-aspartyl]-O-tert-butyl-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-3-cyclopentyl-L-alanine benzyl ester in 10 ml of dimethylformamidewas hydrogenated over 25 mg of 10% palladium/carbon for 3 hours. The catalyst was removed by filtration, the filtrate was evaporated and the residue was triturated with diethyl ether to give 206 mg of N-[N-[N-[N-[N-[3-(tert-butoxycarbonyl)propionyl]-O-tert-butyl-L-α-aspartyl]-O-tert-butyl-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-3-cyclopentyl-L-alanine as a white solid; MS: m/e 944 [M+H].

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-2caf32eaad694a7aae59ccb1e4120172
Source dataset
uspto-grants-1999_02
Patent number
US05866684

Reaction notes

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