Benzyl chloroformate → HCID 57023645, compound

HRID 1632769Notes

Reaction equation

HRID 1632769 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:11][C@@H:12]([C:14]([OH:16])=[O:15])[NH2:13])([O-:3])=[O:2].Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>[OH-].[Na+]>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:11][C@@H:12]([C:14]([OH:16])=[O:15])[NH:13][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 124713S-o-nitrophenyl-L-cysteine

Product 1

HCID 57023645HCID 57023645, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of 48.4 g of S-(o-nitrophenyl)-L-cysteine in 100 ml of 2N aqueous sodium hydroxide at 0° C. is added 28.8 ml of benzyl chloroformate and 50 ml of 4N aqueous sodium hydroxide simultaneously from two addition funnels. The mixture is mechanically stirred overnight at room temperature and then extracted with 150 ml of ether. The aqueous layer is separated and acidified to pH 1 with 12N aqueous hydrochloric acid. The resulting gummy yellow solid is stirred for 3 hr in 500 ml of water, collected by filtration, and dried overnight at 70° C. in vacuo to afford S-(o-nitrophenyl)-N-carbobenzyloxy-L-cysteine; m.p. 84°-88° C.; [α]D =+46.6° (c=1.25, methanol).

Workup

  1. additionsimultaneously from two addition funnels
  2. extractionextracted with 150 ml of ether
  3. customThe aqueous layer is separated
  4. filtrationcollected by filtration
  5. customdried overnight at 70° C. in vacuo

Sources & evidence

ORD record
ord-80366e2412f342cba0461dc340bc9738
Source dataset
uspto-grants-1984_10
Patent number
US04477464

Reaction notes

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