Water → HCID 10305720, compound

HRID 1582731Notes

Reaction equation

HRID 1582731 reaction equation
C(O[C:9](=O)[N:10]([CH:12]([C:16](=[O:59])[NH:17][CH:18]([C:22](=[O:58])[N:23]([CH:25]([CH:54]([CH2:56][CH3:57])[CH3:55])[CH:26]([O:52][CH3:53])[CH2:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][CH:31]1[CH:35]([S:48]([CH3:51])(=[O:50])=[O:49])[CH2:36][C:37](=[O:47])[NH:38][CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:29])[CH3:24])[CH:19]([CH3:21])[CH3:20])[CH:13]([CH3:15])[CH3:14])C)C1C=CC=CC=1.O>CC(O)(C)C.[OH-].[OH-].[Pd+2]>[CH:54]([CH:25]([N:23]([CH3:24])[C:22]([CH:18]([NH:17][C:16](=[O:59])[CH:12]([NH:10][CH3:9])[CH:13]([CH3:15])[CH3:14])[CH:19]([CH3:21])[CH3:20])=[O:58])[CH:26]([O:52][CH3:53])[CH2:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][CH:31]1[CH:35]([S:48]([CH3:51])(=[O:50])=[O:49])[CH2:36][C:37](=[O:47])[NH:38][CH2:39][CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)=[O:29])([CH2:56][CH3:57])[CH3:55]

Participants

5

Reactant 2

HCID 962WaterHCID 69550946HCID 69550946, compound

Product 1

HCID 10305720HCID 10305720, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 6386tert-ButanolSolvent

Procedure

To a stirred solution of the crude {1-[1-({1-sec-butyl-2-methoxy-4-[2-(1-methylsulfonyl-2-phenethylcarbamoyl-ethyl)-pyrrolidin-1-yl]-4-oxo-butyl}-methyl-carbamoyl)-2-methyl-propylcarbamoyl]-2-methyl-propyl}-methyl-carbamic acid benzyl ester (311 mg) obtained above in tBuOH (9 ml) and H2O (1 ml) was added Pd(OH)2 on carbon(ca. 20 wt %, 1 g) at room temperature and then the mixture was set under H2 atmosphere. After being stirred at room temperature for 13.5 hr, the mixture was filtrated through a pad of celite and washed with MeOH. The filtrate and washings were combined and concentrated in vacuo to give the crude gum (285 mg), which was purified by preparative HPLC (column: ODS-80Ts, eluent: 40/30 H2O:CH3CN/0.05% TFA). The appropriate fractions were lyophilized to give the title compound as a white amorphous powder (160 mg, 58%).

Workup

  1. filtrationthe mixture was filtrated through a pad of celite
  2. washwashed with MeOH
  3. concentrationconcentrated in vacuo
  4. customto give the crude gum (285 mg), which
  5. customwas purified by preparative HPLC (column: ODS-80Ts, eluent: 40/30 H2O:CH3CN/0.05% TFA)

Sources & evidence

ORD record
ord-50c0aad808c7433f9d4eb75564a92e0c
Source dataset
uspto-grants-2004_05
Patent number
US06737409B2

Reaction notes

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