N-3-Bromopropylphthalimide → HCID 53928720, compound

HRID 1633272Notes

Reaction equation

HRID 1633272 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:22][CH2:23][CH2:24][N:25]1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35].CC(C)([O-])C.[K+]>CS(C)=O.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:22][CH2:23][CH2:24][N:25]2[C:29](=[O:30])[C:28]3=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]3[C:26]2=[O:35])=[CH:15][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 21611N-3-BromopropylphthalimideHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-HCID 23665647Potassium tert-butoxide

Product 1

HCID 53928720HCID 53928720, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of diphenylmethyl ester of N-tert-butoxycarbonyl-L-tyrosine (447 mg) prepared in Preparation 7 (1), N-(3-bromopropyl)phthalimide (644 mg) and potassium tert-butoxide (268 mg) in dimethyl sulfoxide (7 ml) was stirred for 6 hours at room temperature. The reaction mixture was diluted with water, and extracted with diethyl ether. The extract was washed with water and brine, dried, and evaporated to dryness to give diphenylmethyl ester of N-tert-butoxycarbonyl-O-(3-phthalimidopropyl)-L-tyrosine quantitatively as oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with water and brine
  3. customdried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-78c3998f7ae24f00bde48553f9fb0a84
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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