Sodium borohydride → HCID 67229292, 화합물

HRID 2067856노트

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HRID 2067856 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[C:15]([C@@:17]1([C:37]2([OH:41])[CH2:40][CH2:39][CH2:38]2)[CH2:21][CH2:20][C@@H:19]([N:22](C(=O)C(F)(F)F)[C@@H:23]2[C@H:28]([O:29][CH3:30])[CH2:27][O:26][CH2:25][CH2:24]2)[CH2:18]1)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[C:15]([C@@:17]1([C:37]2([OH:41])[CH2:40][CH2:39][CH2:38]2)[CH2:21][CH2:20][C@@H:19]([NH:22][C@@H:23]2[C@H:28]([O:29][CH3:30])[CH2:27][O:26][CH2:25][CH2:24]2)[CH2:18]1)=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 86654423HCID 86654423, 화합물

생성물 1

HCID 67229292HCID 67229292, 화합물수율 98.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 1.31 g (2.23 mmol) of 1,5-anhydro-3-{[(1R,3S)-3-{[(1S,4S)-5-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]carbonyl}-3-(1-hydroxycyclobutyl)cyclopentyl](trifluoroacetyl)amino}-2,3-dideoxy-4-O-methyl-D-erythro-pentitol and 860 mg (23 mmol) of sodium borohydride in 6.3 mL of ethanol was stirred at ambient temperature for 18 h, then partitioned between water and dichloromethane. The aqueous phase was extracted with additional dichloromethane, and the combined organic phase dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography on silica using 6-15% methanol in dichloromethane afforded 1.08 g (98%) of the title compound as a white foam. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.42-1.47 (m, 9H) 1.56-2.35 (m, 14H) 2.72 (br. s., 1H) 3.11-3.68 (m, 10H) 3.90-3.98 (m, 1H) 4.08 (dd, J=12.6, 2.7 Hz, 1H) 4.38-4.58 (m, 1H) 4.84-5.16 (m, 1H). LC-MS ES+ 494.3. HRMS calculated for C26H43N3O6: 494.3230; found: 494.3260.

후처리

  1. custompartitioned between water and dichloromethane
  2. extractionThe aqueous phase was extracted with additional dichloromethane
  3. dry with materialthe combined organic phase dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-100e51c756a64de3b7562c731bf9333e
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293903B2

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