1,3,2,4-Dithiadiphosphetane, 2,4-bis(methylthio)-, 2,4-disulfide → (S)-methyl 3,4-dihydro-2,8-diisopropyl-3-thioxo-2H-1,4-benzoxazine-4-acetate

HRID 622371노트

반응식

HRID 622371 반응식
[CH:1]([C@H:4]1[C:9](=O)[N:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:7]2[CH:16]=[CH:17][CH:18]=[C:19]([CH:20]([CH3:22])[CH3:21])[C:6]=2[O:5]1)([CH3:3])[CH3:2].C[S:24]P1(=S)SP(=S)(SC)S1>C1(C)C=CC=CC=1>[CH:1]([C@H:4]1[C:9](=[S:24])[N:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:7]2[CH:16]=[CH:17][CH:18]=[C:19]([CH:20]([CH3:22])[CH3:21])[C:6]=2[O:5]1)([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 45209581,3,2,4-Dithiadiphosphetane, 2,4-bis(methylthio)-, 2,4-disulfideHCID 14234720(S)-methyl 3,4-dihydro-2,8-diisopropyl-3-oxo-2H-1,4-benzoxazine-4-acetate

생성물 1

HCID 22839825(S)-methyl 3,4-dihydro-2,8-diisopropyl-3-thioxo-2H-1,4-benzoxazine-4-acetate수율 93.5%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
50 °C

실험 절차

A mixture of (S)-methyl 3,4-dihydro-2,8-diisopropyl-3-oxo-2H-1,4-benzoxazine-4-acetate (3.05 g), 2,4-bis (methylthio)-1,3,2,4-dithiadiphosphetan-2,4-disulfide (Davy reagent methyl)(2.84 g) and toluene (60 ml) was stirred at 50° C. for 64 hours. The insoluble material was filtered off and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (100 g) using hexane-ethyl ether (85:15, v/v) as the eluent to yield (S)-methyl 3,4-dihydro-2,8-diisopropyl-3-thioxo-2H-1,4-benzoxazine-4-acetate as an oil (3.00 g).

후처리

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography on silica gel (100 g)

출처 및 근거

ORD 기록
ord-197c87abe532419fa93d5c5c3b370478
출처 데이터셋
uspto-grants-1988_09
특허 번호
US04771050

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