Phthalimide → tert-butyl-2(R)-[(tert-butoxycarbonyl)amino]-3-phthalimidopropionate

HRID 2297998Notes

Reaction equation

HRID 2297998 reaction equation
[C:1]([O:5][CH2:6][C@H:7]([C:16](O)=O)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].[C:19]1(=[O:29])[NH:23][C:22](=[O:24])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=[O:52]>O1CCCC1>[C:1]([O:5][C:6](=[O:52])[C@H:7]([NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:16][N:23]1[C:19](=[O:29])[C:20]2=[CH:28][CH:27]=[CH:26][CH:25]=[C:21]2[C:22]1=[O:24])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 6992546(R)-3-(tert-Butoxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

Product 1

HCID 18337585tert-butyl-2(R)-[(tert-butoxycarbonyl)amino]-3-phthalimidopropionateYield 62.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of O-tert-butyl-N-BOC-D-serine (4 g, 15.31 mmol), phthalimide (3.38 g, 22.9 mmol) and triphenyl phosphine (6.03 g, 22,9 mmol) in tetrahydrofuran (120 ml, anhydrous) was added diisopropyl azodicarboxylate (4.5 ml, 22.9 mmol). The mixture was stirred under nitrogen atmosphere over night. The tetrahydrofuran was removed on the roto-evaporator and the remainder was taken up in methylene chloride (60 ml) and loaded onto a flash silica gel column. Elution with ethyl acetate/hexanes (19%) gave tert-butyl-2(R)-[(tert-butoxycarbonyl)amino]-3-phthalimidopropionate (3.74 g) as a white powder.

Workup

  1. customThe tetrahydrofuran was removed on the roto-evaporator
  2. washElution with ethyl acetate/hexanes (19%)

Sources & evidence

ORD record
ord-30149d8a8e534d8ea12d16344bcf7527
Source dataset
uspto-grants-2002_12
Patent number
US06492394B1

Reaction notes

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