Sulfuric Acid → HCID 67462821, 화합물

HRID 915750노트

반응식

[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([C:29]([OH:31])=[O:30])[CH2:20][O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(OC[CH2:37][CH2:38][CH3:39])(=O)C.S(=O)(=O)(O)O.Cl[CH2:46]Cl>>[C:38]([O:30][C:29](=[O:31])[C@@H:19]([CH2:20][O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[NH:18][C:16]([O:15][CH2:14][CH:12]1[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:17])([CH3:37])([CH3:39])[CH3:46]

참가 물질

반응물 4

HCID 1118Sulfuric Acid

HCID 6344Dichloromethane

HCID 31272Butyl Acetate

HCID 7019719Fmoc-D-Ser(Bzl)-OH

생성물 1

HCID 67462821HCID 67462821, 화합물수율 77%

실험 절차

N-[(9H-Fluoren-9-yl)methoxycarbonyl]-O-(benzyl)-D-serine (0.710 g, 1.70 mmole) in dichloromethane (8 mL) was treated with 1-butyl acetate (3 mL) and concentrated sulfuric acid (40 μL) in a sealed flask at 0° C. Upon completion (TLC), the reaction was quenched with of dichloromethane (10 mL) and saturated aqueous potassium bicarbonate (15 mL). The organic layer was washed with distilled water, and evaporated. The resulting residue was purified by flash column chromatography (98:2 dichloromethane/methanol) to yield the title compound as a colorless oil (0.292 g, 77%);

후처리

customUpon completion (TLC), the reaction was quenched with of dichloromethane (10 mL) and saturated aqueous potassium bicarbonate (15 mL)
washThe organic layer was washed with distilled water
customevaporated
customThe resulting residue was purified by flash column chromatography (98:2 dichloromethane/methanol)

출처 및 근거

ORD 기록: ord-ae480f33f6ff4297aab2e326c73e53a7
출처 데이터셋: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07268125B2

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