Sodium borohydride → HCID 67229292、化合物

HRID 1844320ノート

反応式

HRID 1844320 の反応式
[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]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 86654423HCID 86654423、化合物

生成物 1

HCID 67229292HCID 67229292、化合物収率 98.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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 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.

後処理

  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

出典と根拠

ORDレコード
ord-c95af676cb28412db6906e7db6a2b6d5
出典データセット
uspto-grants-2015_02
特許番号
US08946413B2

反応ノート

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