Ethyl Acetate → N-[(1,1-Dimethylethoxy)carbonyl]-L-homoserine cyclopentyl ester

HRID 1009960Notes

Reaction equation

[CH:1]1([O:6][C:7](=[O:27])[C@@H:8]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:9][CH2:10][O:11][Si](C(C)(C)C)(C)C)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(OCC)(=O)C>C(O)(=O)C.C1COCC1.O>[CH:1]1([O:6][C:7](=[O:27])[C@@H:8]([NH:19][C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:9][CH2:10][OH:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 30 °C

Procedure

(S)-2-tert-Butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid cyclopentyl ester (1.57 g, 3.9 mmol) was dissolved in acetic acid:THF:water (3:1:1, 100 ml). The reaction mixture was stirred at 30° C. for 16 hours for complete reaction. Ethyl acetate (200 ml) was added and washed with 1M Na2CO3, 1M HCl and brine. The ethyl acetate extracts were dried over magnesium sulphate and evaporated under reduced pressure to give the product as a clear oil which crystallised on standing (1.0 g, 95%). LCMS purity 100%, m/z 310.3 [M++Na], 1H NMR (300 MHz, CDCl3), δ: 5.40 (1 H, d, J=6.5 Hz), 5.20 (1 H, m), 4.40 (1H, m), 3.65 (2H, m), 2.15 (1H, m), 1.90-1.55 (9H, bm), 1.45 (9H, s).

Workup

washwashed with 1M Na2CO3, 1M HCl and brine
dry with materialThe ethyl acetate extracts were dried over magnesium sulphate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-252aa3549e20432788b5f037a5d247f1
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973181B2

Reaction notes

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