methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-4-phenylbutanoate → Boc-homophenylalaninal

HRID 2072667Notes

Reaction equation

C[O:2][C:3](=O)[C@H:4]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]>C1(C)C=CC=CC=1>[C:6]([NH:5][C@H:4]([CH:3]=[O:2])[CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:7]

Participants

Conditions

Temperature: -80 °C

Procedure

2.93 g of N-BOC homo phenylalanine methyl ester (10 mmol) are dissolved in 25 ml of absolute toluene under nitrogen and the solution is cooled to -80° C. 20 ml of -20% strength DIBA in toluene are added dropwise and the temperature maintained. Since the reaction was not complete after 1.5 h a further 3 ml of 20% strength DIBA were added.

Workup

temperaturethe temperature maintained
additiona further 3 ml of 20% strength DIBA were added

Sources & evidence

ORD record: ord-152a117c7af2493ba3bd35e0ffadc29a
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04914087

Reaction notes

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