4-Methylmorpholine → HCID 70002199, compound

HRID 1264394Notes

Reaction equation

HRID 1264394 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:23]([OH:25])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.[B-](F)(F)(F)F.CN(C(ON1[C:51](=O)[CH:50]=[CH:49][CH:48]=[CH:47]1)=[N+](C)C)C.Cl.C([O:61]C(=O)CNC)C1C=CC=CC=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:23](=[O:25])[N:27]([CH2:32][C:31]([O:30][CH2:29][C:28]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:61])[CH3:26])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 18618415Benzyl N-methylglycinate--hydrogen chloride (1/1)HCID 69429791HCID 69429791, compound

Product 1

HCID 70002199HCID 70002199, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 g (54.4 mmol) (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester in 1.5 1 CH2Cl2 were treated with 6.6 ml (60 mmol, 1.1 eq) 4-methyl morpholine, 19.4 g (65.3 mmol, 1.2 eq) TPTU and 12.7 g (59.8 mmol) sarcosine benzylester-hydrochloride. The mixture was stirred at RT for 39 h, was concentrated and purified by column chromatography with EtOAc:CH2Cl2 4:1 as eluent yielding 14.2 g (50%) (2S,4R)-2-(benzyloxycarbonylmethyl-methyl-carbamoyl)-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester.

Workup

  1. concentrationwas concentrated
  2. custompurified by column chromatography with EtOAc:CH2Cl2 4:1 as eluent

Sources & evidence

ORD record
ord-f17725a0371d43a6a7e8546b4d1b11dd
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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