Acetic Acid → HCID 70023704, compound

HRID 1359027Notes

Reaction equation

HRID 1359027 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C@H:4]([CH2:25][CH:26]=C)[CH2:5][C@@H:6]([NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[C:29](O)(=[O:31])C.CSC>CO.C(Cl)Cl.C(Cl)Cl>[CH3:1][O:2][C:3]([C@@H:4]1[CH2:25][CH:26]([O:31][CH3:29])[N:14]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[C@@H:6]([C:7]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])[CH2:5]1)=[O:28]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 1068Dimethyl SulfideHCID 53916592HCID 53916592, compound

Product 1

HCID 70023704HCID 70023704, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Ozone gas was bubbled through a stirred, cold, (−78° C.) solution of (2R,4R)-4-allyl-2-benzyloxycarbonylamino-pentanedioic acid 1-tert-butyl ester 5-methyl ester (5.0 g, 12.8 mmol) in 100 mL of 10:1 methanol/methylene chloride, and 0.73 mL of acetic acid until a blue color persisted. Nitrogen gas was then bubbled through the solution until the blue color dissipated. The mixture was warmed to ambient temperature and dimethyl sulfide (2.8 mL, 3.83 mmol) was added. The mixture was stirred for 48 hours, diluted with methylene chloride, and washed with 10% aqueous sodium carbonate, brine, and the mixture was dried over sodium sulfate. Filtration and concentration of the filtrate provided (2R,4S)-6-methoxy-piperidine-1,2,4-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester 4-methyl ester as a clear oil, which was used in the subsequent step without purification.

Workup

  1. customOzone gas was bubbled through a stirred
  2. customNitrogen gas was then bubbled through the solution until the blue color
  3. washwashed with 10% aqueous sodium carbonate, brine
  4. dry with materialthe mixture was dried over sodium sulfate
  5. filtrationFiltration and concentration of the filtrate

Sources & evidence

ORD record
ord-8a5d4e03db0746eab1c9c982dd888782
Source dataset
uspto-grants-2003_07
Patent number
US06599890B1

Reaction notes

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