Methanesulfonyl chloride → N-Benzyloxycarbonyl-N-[2-(methanesulphonyloxy)ethyl]-glycine tert-butyl ester

HRID 54617Notes

Reaction equation

HRID 54617 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][N:8]([C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:9][CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2].[CH3:23][S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:22])[CH2:7][N:8]([C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[CH2:9][CH2:10][O:11][S:24]([CH3:23])(=[O:26])=[O:25])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 19959626Tert-butyl 2-{[(benzyloxy)carbonyl](2-hydroxyethyl)amino}acetate

Product 1

HCID 19959619N-Benzyloxycarbonyl-N-[2-(methanesulphonyloxy)ethyl]-glycine tert-butyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The product from Example 5 (14.4 g; 47 mmol) is reacted in anhydrous pyridine (270 ml) with methanesulphonyl chloride (4.47 ml; 58 mmol) and then worked up as described in Example 2. Yield: 14.7 g (82%), brown oil.

Sources & evidence

ORD record
ord-759f8f5b90184a7bb32ee67fbd5b1723
Source dataset
uspto-grants-1997_04
Patent number
US05623049

Reaction notes

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