Benzyl chloroformate → HCID 21967721, compound

HRID 1637900Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH:7]=[N:8][C@H:9]([C:14]([O-:16])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:5][CH:4]=1.[Na+].Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>>[CH2:24]([O:23][C:21]([N:8]1[C@@H:9]([CH2:10][CH:11]([CH3:13])[CH3:12])[C:14](=[O:16])[O:15][C@H:7]1[C:6]1[CH:17]=[CH:18][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Reactant 2

HCID 10387Benzyl chloroformate

HCID 70300704HCID 70300704, compound

Product 1

HCID 21967721HCID 21967721, compound

Procedure

(2S,4S)-N-Benzyloxycarbonyl-4-isobutyl-2-(4'-methoxyphenyl)-1,3-oxazolidin-5-one (15) was prepared from sodium N-(para-methoxybenzylidene)-(L)-leucinate (2.71 g, 10.0 mM) and benzyl chloroformate (1.43 mL, 10.0 mM) following general procedure C and obtained as a colourless oil after purification by flash column chromatography, using 25% ethyl acetate/petrol as eluant (3.21 g, 84%, single diastereomer): [α]D20 -30.0 (c 1.0, CHCl3); IR (CHCl3): 1795, 1715 cm-1 ; 1H NMR (200 MHz, CDCl3): δ 6.89-7.38 (m, 9H), 6.71 (s, 1H), 5.20 (s, 2H), 4.47 (t, J=7 Hz, 1H), 3.82 (s, 3H), 1.57-1.98 (m, 3H), 0.88-0.92 (m, 6H); 13C NMR (50.3 MHz, CDCl3): δ 172.5, 160.4, 154.0, 135.3, 129.2, 128.6, 128.3, 127.4, 113.9, 88.8, 68.1, 55.3, 54.4, 42.1, 24.5, 22.3, 22.2; LRMS (NH3): 384 (MH+); HRMS: calcd for C22H26NO5 (MH+): 384.1811; found: 384.1811.

Workup

customobtained as a colourless oil
customafter purification by flash column chromatography

Sources & evidence

ORD record: ord-50539290970848dcb27983750b602594
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06043278

Reaction notes

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