Triphenylphosphine → benzyl (3R)-3-t-butoxycarbonylamino-4-(5-cyano-2-benzyloxyphenoxy)butanoate

HRID 2414424Notes

Reaction equation

HRID 2414424 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:21][OH:22])[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:23]([O:30][C:31]1[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][C:32]=1O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:21][O:22][C:38]1[CH:37]=[C:34]([C:35]#[N:36])[CH:33]=[CH:32][C:31]=1[O:30][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11045079Boc-D-aspartinol 4-Benzyl EsterHCID 154534514-(Benzyloxy)-3-hydroxybenzonitrile

Product 1

HCID 86584114benzyl (3R)-3-t-butoxycarbonylamino-4-(5-cyano-2-benzyloxyphenoxy)butanoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4.8 g (15.5 mmol) of benzyl (3R)-3-t-butoxycarbonylamino-4-hydroxybutanoate was dissolved in 100 ml of tetrahydrofuran. 2.9 g (12.9 mmol) of 4-benzyloxy-3-hydroxybenzonitrile, 4.1 g (15.5 mmol) of triphenylphosphine and 6.7 g (15.5 mmol) of diethyl azodicarboxylate were added to the obtained solution under cooling with ice, and they were stirred at room temperature overnight. After the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. temperatureunder cooling with ice, and they
  2. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-acc9ea13c03d4b56adc82941b174753c
Source dataset
uspto-grants-2004_11
Patent number
US06812231B2

Reaction notes

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