HCID 178451023, compound → HCID 178451024, compound

HRID 1289257Notes

Reaction equation

HRID 1289257 reaction equation
C(OC([NH:11][C@@:12]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:33]([OH:35])=[O:34])[CH2:13][CH2:14][C:15]([NH:17][C@@H:18]([C:28]1[NH:32][N:31]=[N:30][N:29]=1)[CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:16])=O)C1C=CC=CC=1>C(O)C.[Pd]>[C:36]([C@:12]([C:33]([OH:35])=[O:34])([CH2:13][CH2:14][C:15]([NH:17][C@@H:18]([C:28]1[NH:32][N:31]=[N:30][N:29]=1)[CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])=[O:16])[NH2:11])([CH3:37])([CH3:38])[CH3:39]

Participants

4

Reactant 1

HCID 178451023HCID 178451023, compound

Product 1

HCID 178451024HCID 178451024, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

A solution of tert-butyl (4R)-4-{N-[N-(benzyloxycarbonyl)-αtert-butyl-(S)-γ-glutamyl]amino}-4-(tetrazol-5-yl)butyrate (0.320 g, 0.585 mmol) in ethanol (35 ml) was stirred with 10% Pd-C. (0.12 g) under a hydrogen atmosphere at ambient temperature. After 16 hours further 10% Pd-C. (0.09 g) was added and the mixture was stirred under hydrogen for a further 6 hours. It was then filtered through Celite and the filtrate was evaporated. Several portions of dichloromethane were added and evaporated to leave tert-butyl (4R)-4-[N-(α-tert-butyl-(S)-γ-glutamyl)amino]-4-(tetrazol-5-yl)butyrate as a crisp, colourless glass which was dried over phosphorus pentoxide and used without further purification. Yield 0.24 g; m.p. 92°-94° C.

Workup

  1. customat ambient temperature
  2. addition(0.09 g) was added
  3. filtrationIt was then filtered through Celite
  4. customthe filtrate was evaporated
  5. additionSeveral portions of dichloromethane were added
  6. customevaporated

Sources & evidence

ORD record
ord-143e9a10dba040e482c45ccd8a811331
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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