Glycine → O-Benzyl-N-(tert-butoxycarbonyl)-L-serylglycine

HRID 1590967

Reaction equation

HRID 1590967 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].C(=O)([O-])O.[Na+].[NH:11]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@H:12]([C:22](ON1C(=O)CCC1=O)=[O:23])[CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[NH:11]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@H:12]([C:22]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:23])[CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 750GlycineHCID 516892Sodium BicarbonateHCID 12879025Boc-Ser(Bzl)-OSu

Product 1

HCID 14608022O-Benzyl-N-(tert-butoxycarbonyl)-L-serylglycine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an aqueous solution containing 6.80 g of H-Gly-OH and 9.20 g of sodium hydrogen carbonate, under ice-cooling condition, was added 120 ml of THF solution containing 27.5 g of Boc-Ser(Bzl)-OSu, and the mixture was stirred at room temperature overnight.

Workup

  1. temperatureunder ice-cooling condition

Sources & evidence

ORD record
ord-f981639275ce4afcb212119f5339d2a8
Source dataset
uspto-grants-1993_04
Patent number
US05204326

Linked notes

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