N-(1-benzyloxycarbonyloxy-3,3-dimethylbut-2(R)-yl)-3(R)-[3-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acid benzyl ester → N-(2,2-dimethyl-1(S)-hydroxymethyl-propyl)-3(R)-[3-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acid

HRID 382160Notes

Reaction equation

HRID 382160 reaction equation
C([O:8][C:9](=[O:49])[CH2:10][C@@H:11]([N:32]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][C:40]([C:43]3[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=3)=[CH:39][CH:38]=2)=[CH:33]1)[C:12]([NH:14][C@H:15]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:16][O:17]C(OCC1C=CC=CC=1)=O)=[O:13])C1C=CC=CC=1>CO.CCOC(C)=O.[OH-].[OH-].[Pd+2]>[CH3:29][C:28]([CH3:31])([CH3:30])[C@H:15]([NH:14][C:12](=[O:13])[C@H:11]([N:32]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][C:40]([C:43]3[CH:44]=[CH:45][N:46]=[CH:47][CH:48]=3)=[CH:39][CH:38]=2)=[CH:33]1)[CH2:10][C:9]([OH:49])=[O:8])[CH2:16][OH:17]

Participants

5

Reactant 1

HCID 54275701N-(1-benzyloxycarbonyloxy-3,3-dimethylbut-2(R)-yl)-3(R)-[3-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acid benzyl ester

Product 1

HCID 15487948N-(2,2-dimethyl-1(S)-hydroxymethyl-propyl)-3(R)-[3-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acidYield 95%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(1-benzyloxycarbonyloxy-3,3-dimethylbut-2(R)-yl)-3(R)-[3-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acid benzyl ester (140 mg, 0.212 mmol) and Pd(OH)2 (60 mg of 20% Pd by content) in MeOH (1mL) and EtOAc (9 mL) was stirred under H2 atmosphere for 3 hours. The catalyst was filtered onto Celite and rinsed with 10% MeOH/CHCl3 (75 mL). The filtrate was concentrated in vacuo to provide a yellow solid, which was precipitated from hot CHCl3 solution with hexane to furnish 68 mg (95%) of N-[2,2-dimethyl-1(S)-(hydroxymethyl)propyl]-3(R)-[3-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acid as a yellow solid, mp 192-4° C.

Workup

  1. filtrationThe catalyst was filtered onto Celite
  2. washrinsed with 10% MeOH/CHCl3 (75 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto provide a yellow solid, which
  5. customwas precipitated from hot CHCl3 solution with hexane

Sources & evidence

ORD record
ord-4138e3228deb4190b3ba7430c7ff9a5c
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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