N-((Phenylmethoxy)carbonyl)-O-(phenylmethyl)-L-serine → N-(Benzyloxycarbonyl)-O-benzylserine, t-butyl ester

HRID 1264571Notes

Reaction equation

HRID 1264571 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:22]([OH:24])=[O:23])[CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:22]([O:24][C:2]([CH3:7])([CH3:3])[CH3:1])=[O:23])[CH2:13][O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 6993425N-((Phenylmethoxy)carbonyl)-O-(phenylmethyl)-L-serine

Product 1

HCID 15778647N-(Benzyloxycarbonyl)-O-benzylserine, t-butyl esterYield 199.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of 25 g (0.076 mol) of N-(benzyloxycarbonyl)-O-benzylserine in 600 ml of CH2Cl2 cooled to −6° C. in an ice-salt bath was bubbled isobutylene, while 4.1 ml of concentrated sulfuric acid was added dropwise thereto. The mixture was stirred for 4 hours and worked up as described in Synthetic Commun., 26:2723 (1996) to give 29.24 g of product as a yellow oil.

Workup

  1. customwas bubbled isobutylene
  2. additionwhile 4.1 ml of concentrated sulfuric acid was added dropwise

Sources & evidence

ORD record
ord-4bf99985c3f94612ad2fe2b13a2402c1
Source dataset
uspto-grants-2003_04
Patent number
US06544984B1

Reaction notes

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