Oxalate → HCID 54290134, compound

HRID 1194963Notes

Reaction equation

HRID 1194963 reaction equation
C([BH3-])#N.[Na+].[C:5]([O:9][C:10](=[O:21])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:20])[C@H:17]([CH3:19])[NH2:18])([CH3:8])([CH3:7])[CH3:6].C([O-])(=O)C([O-])=O.C([O-])(=O)C.[Na+].[CH2:33]([O:40][C:41]([N:43]1[CH2:48][CH2:47][CH:46]([CH2:49][CH2:50][CH2:51][CH2:52][C:53](=O)[C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH2:45][CH2:44]1)=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(O)C.C(O)(=O)C>[C:5]([O:9][C:10](=[O:21])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:20])[C@H:17]([CH3:19])[NH:18][CH:53]([C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH2:52][CH2:51][CH2:50][CH2:49][CH:46]1[CH2:47][CH2:48][N:43]([C:41]([O:40][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:42])[CH2:44][CH2:45]1)([CH3:6])([CH3:8])[CH3:7]

Participants

8

Reactant 5

HCID 71081OxalateHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 12939800tert-Butyl L-alanyl-L-prolinateHCID 13817563Ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-oxohexanoate

Product 1

HCID 54290134HCID 54290134, compoundYield 13.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×

Procedure

A solution of 0.57 g of sodium cyanoborohydride in 40 ml of ethanol is added dropwise to a stirred mixture of 2 g of N-(L-alanyl)-L-proline tert-butyl ester. oxalate, 1 of sodium acetate, 0.72 g of acetic acid, 10 g of molecular sieves 3A, 3.4 g of ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-oxohexanoate and 50 ml of ethanol at room temperature over a period of 2 hours. The reaction mixture is allowed to stand overnight and filtered, and the filtrate is concentrated under reduced pressure. The resulting oily material is purified by silica gel column chromatography (hexane:ethyl acetate=1:1 to hexane:acetone=1:1) to give 0.66 g of N-[N-[5-(1-benzyloxycarbonyl-4-piperidyl)-1-ethoxycarbonylpentyl]-L-alanyl]-L-proline tert-butyl ester as a colorless oil.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe resulting oily material is purified by silica gel column chromatography (hexane:ethyl acetate=1:1 to hexane:acetone=1:1)

Sources & evidence

ORD record
ord-6f35ada4834d404a8053fc4eaad5aac6
Source dataset
uspto-grants-1989_03
Patent number
US04816466

Reaction notes

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