N-Methylmorpholine N-oxide monohydrate → 4-((S)-2-Benzyloxycarbonylamino-4,5-dihydroxy-pentanoyl)-piperazine-1-carboxylic acid ethyl ester

HRID 1970496Notes

Reaction equation

HRID 1970496 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:28])[C@@H:13]([NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14][CH:15]=[CH2:16])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[OH2:29].C[N+]1([O-])CCOCC1.OS([O-])=O.[Na+].CC(C)=O.[OH2:47]>O=[Os](=O)(=O)=O>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12](=[O:28])[C@@H:13]([NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14][CH:15]([OH:47])[CH2:16][OH:29])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 18366337Propan-2-one--water (1/1)HCID 23665763Sodium BisulfiteHCID 668557364-((S)-2-Benzyloxycarbonylamino-pent-4-enoyl)-piperazine-1-carboxylic acid ethyl ester

Product 1

HCID 668551894-((S)-2-Benzyloxycarbonylamino-4,5-dihydroxy-pentanoyl)-piperazine-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of 640 mg 4-((S)-2-Benzyloxycarbonylamino-pent-4-enoyl)-piperazine-1-carboxylic acid ethyl ester in 10 ml acetone/water (4/1) were added 2.1 ml OsO4 (2.5 w/w in t-BuOH) and 567 mg 4-Methylmorpholine-N-oxide monohydrate at 0° C. After 1 h solid NaHSO3 was added, the suspension stirred for 5 minutes, filtered and the filtrate concentrated. The residue was redissolved in dichloromethane and washed with aqueous NaHSO3 (5%) and brine. The crude product obtained after evaporation of the solvent was directly used in the next reaction step. Yield: 755 mg.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated
  3. dissolutionThe residue was redissolved in dichloromethane
  4. washwashed with aqueous NaHSO3 (5%) and brine

Sources & evidence

ORD record
ord-3102e9c913594831b2be54300b072b10
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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