Oxalate → HCID 11765114, compound

HRID 1031795Notes

Reaction equation

HRID 1031795 reaction equation
C([BH3-])#N.[Na+].[C:5]([O:9][C:10](=[O:27])[CH2:11][N:12]([C:22](=[O:26])[C@H:23]([CH3:25])[NH2:24])[CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14]1)([CH3:8])([CH3:7])[CH3:6].C([O-])(=O)C([O-])=O.C([O-])(=O)C.[Na+].[CH2:39]([O:46][C:47]([N:49]1[CH2:54][CH2:53][CH:52]([CH2:55][CH2:56][CH2:57][CH2:58][C:59](=O)[C:60]([O:62][CH2:63][CH3:64])=[O:61])[CH2:51][CH2:50]1)=[O:48])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(O)C.C(O)(=O)C>[C:5]([O:9][C:10](=[O:27])[CH2:11][N:12]([C:22](=[O:26])[C@H:23]([CH3:25])[NH:24][C@@H:59]([C:60]([O:62][CH2:63][CH3:64])=[O:61])[CH2:58][CH2:57][CH2:56][CH2:55][CH:52]1[CH2:53][CH2:54][N:49]([C:47]([O:46][CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[O:48])[CH2:50][CH2:51]1)[CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14]1)([CH3:6])([CH3:8])[CH3:7]

Participants

8

Reactant 5

HCID 71081OxalateHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 13132288HCID 13132288, compoundHCID 13817563Ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-oxohexanoate

Product 1

HCID 11765114HCID 11765114, compoundYield 8.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×

Procedure

A solution of 0.6 g of sodium cyanoborohydride in 50 ml of ethanol is added dropwise to a stirred mixture of 2 g of N-(L-alanyl)-N-(2-indanyl)glycine tert-butyl ester.oxalate, 0.78 g of sodium acetate, 0.58 g of acetic acid, 10 g of molecular sieves 3 A, 3.6 g of ethyl 6-(1-benzyloxycarbonyl-4-piperidyl)-2-oxohexanoate and 50 ml of ethanol at room temperature over a period of 3 hours. The reaction solution is allowed to stand overnight and filtered, and the filtrate is concentrated under reduced pressure. The residue is diluted with 50 ml of water and extracted with 200 ml of ethyl acetate. The extract is dried and concentrated under reduced pressure. The resulting oily material is separated and purified by silica gel column chromatography (hexane:ethyl acetate=1:1 to 2:3), whereby the first fraction yields 0.35 g of N-[N-[(R)-5-(1-benzyloxycarbonyl-4-piperidyl)-1-ethoxycarbonylpentyl]-L-alanyl]-N-(indan-2-yl)glycine tert-butyl ester as a colorless oil.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. additionThe residue is diluted with 50 ml of water
  4. extractionextracted with 200 ml of ethyl acetate
  5. customThe extract is dried
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting oily material is separated
  8. custompurified by silica gel column chromatography (hexane:ethyl acetate=1:1 to 2:3), whereby the first fraction

Sources & evidence

ORD record
ord-6d287a13e52941c59a17d6024226cacd
Source dataset
uspto-grants-1990_09
Patent number
US04954625

Reaction notes

Loading…