Acetic Acid → HCID 57495630, 화합물

HRID 1092345노트

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HRID 1092345 반응식
Cl.[NH2:2][CH:3]1[CH:10]2[CH2:11][C:6]3([OH:14])[CH2:7][C:8]([OH:13])([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2.[C:15]([NH:22][C:23]1([CH:28]=O)[CH2:27][CH2:26][CH2:25][CH2:24]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(O)(=O)C.C([O-])(O)=O.[Na+]>CO.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>[C:18]([O:17][C:15](=[O:16])[NH:22][C:23]1([CH2:28][NH:2][CH:3]2[CH:10]3[CH2:9][C:8]4([OH:13])[CH2:7][C:6]([OH:14])([CH2:5][CH:4]2[CH2:12]4)[CH2:11]3)[CH2:24][CH2:25][CH2:26][CH2:27]1)([CH3:21])([CH3:19])[CH3:20]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 16217741tert-Butyl (1-formylcyclopentyl)carbamateHCID 57495631HCID 57495631, 화합물

생성물 1

HCID 57495630HCID 57495630, 화합물수율 56%

시약·촉매·용매 2

HCID 887Methanol용매HCID 5049666Sodium triacetoxyborohydride용매

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온도
60 °C

실험 절차

To a mixture of 6-amino-adamantane-1,3-diol hydrochloride (258 mg, J. Med. Chem. 50, 2007, 149), N-Boc-cycloleucinal (250 mg) and acetic acid (0.67 ml) in MeOH (5.0 ml), sodium triacetoxyborohydride was added at room temperature. The mixture was stirred at 60° C. for 30 min. The mixture was basified with saturated NaHCO3 solution. The mixture was extracted with AcOEt, washed with brine, dried over MgSO4 and evaporated. The residue was purified with silica gel chromatography (CH2Cl2:MeOH:NH4OH=from 100:0:0 to 90:9:1) to obtain the title compound (250 mg, 56%) as a white amorphous.

후처리

  1. additionwas added at room temperature
  2. extractionThe mixture was extracted with AcOEt
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified with silica gel chromatography (CH2Cl2:MeOH:NH4OH=from 100:0:0 to 90:9:1)

출처 및 근거

ORD 기록
ord-3f6498360f464d6caefacd9f6a365a9a
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129423B2

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