Benzyl chloroformate → HCID 21967719, compound

HRID 1637899Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH:7]=[N:8][C@H:9]([C:11]([O-:13])=[O:12])[CH3:10])=[CH:5][CH:4]=1.[Na+].Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>>[CH2:21]([O:20][C:18]([N:8]1[C@@H:9]([CH3:10])[C:11](=[O:13])[O:12][C@H:7]1[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:15][CH:14]=1)=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Reactant 2

HCID 10387Benzyl chloroformate

HCID 70299618HCID 70299618, compound

Product 1

HCID 21967719HCID 21967719, compound

Procedure

(2S,4S)-N-Benzyloxycarbonyl-2-(4'-methoxyphenyl)-4-methyl-1,3-oxazolidin-5-one (14) was prepared from sodium N-(para-methoxybenzylidene)-(L)-alaninate (2.29 g, 10.0 mM) and benzyl chloroformate (1.43 mL, 10.0 mM) following general procedure C and obtained as a white solid after purification by flash column chromatography, using 33% ethyl acetate/petrol as eluant (1.75g, 51%, single diastereomer): [α]D20 +99.9 (c 1.0, CHCl3); mp 97-99° C.; IR (KBr): 1790, 1695 cm-1 ; 1H NMR (500 MHz, d8 -toluene, 90° C.): δ 6.56-7.06 (m, 9H), 6.11 (s, 1H), 4.82 (d, J=12 Hz, 1H), 4.72 (d, J=12 Hz, 1H), 4.13 (q, J=7 Hz, 1H), 3.35 (s, 3H), 1.47 (d, J=7 Hz, 3H); 13C NMR (50.3 MHz, CDCl3): δ 172.3, 160.8, 152.0, 135.2, 128.4, 128.0, 127.7, 125.8, 121.3, 114.1, 89.2, 67.5, 55.3, 52.1, 16.5; LRMS (NH3): 342 (MNH4+). Anal. Calcd for C19H19NO5 : C, 66.85; H, 5.61; N, 4.10; found: C, 66.80; H, 5.42; N, 4.15.

Workup

customobtained as a white solid
customafter purification by flash column chromatography

Sources & evidence

ORD record: ord-31e80ee9fa80479abe1dbb840f8e8a68
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06043278

Reaction notes

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