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4-Methylmorpholine → 1-[(R)-Isopropoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid methyl ester

HRID 2304308
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HRID 2304308 반응식
[CH:1]([O:4][C:5]([NH:7][C@H:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:9]([OH:11])=O)=[O:6])([CH3:3])[CH3:2].Cl.[CH3:19][O:20][C:21](=[O:27])[C@@H:22]1[CH2:26][CH2:25][CH2:24][NH:23]1.CN1CCOCC1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O.O>[CH3:19][O:20][C:21]([C@@H:22]1[CH2:26][CH2:25][CH2:24][N:23]1[C:9](=[O:11])[C@H:8]([NH:7][C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[O:6])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:27]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 2733200methyl L-prolinate hydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 53741285(R)-Isopropoxycarbonylamino-phenyl-acetic acid

생성물 1

HCID 545024061-[(R)-Isopropoxycarbonylamino-phenyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid methyl ester수율 91%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of (R)-Isopropoxycarbonylamino-phenyl-acetic acid (0.74 g), (L)-proline methyl ester hydrochloride (0.51 g), N-methyl morpholine (1.00 mL) and 1.00 g of 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) in 10 mL of dry N,N-dimethyl formamide was stirred for 3 h at ambient temperature. The volatiles were pumped off and water was added followed by extraction with ethyl acetate and concentration of the organic layer. The remaining residue was purified by silica chromatography (ethyl acetatelisohexane=3/1) to give 0.95 g (91%) of the title compound as a colorless oil. (+)-APCI-MS: 349 (MH+).

후처리

  1. extractionfollowed by extraction with ethyl acetate and concentration of the organic layer
  2. customThe remaining residue was purified by silica chromatography (ethyl acetatelisohexane=3/1)

출처 및 근거

ORD 기록
ord-886849a7fd884908986a9f7baeeea67d
출처 데이터셋
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06432955B1

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