Acetic Acid → Benzyl ((2S,3R)-1-(4-((tert-butyloxycarbonylamino)methyl)phenyl)-3-hydroxy-4-methylpent-4-en-2-yl)carbamate

HRID 1253411노트

반응식

HRID 1253411 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C@H:17]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:18](=[O:22])[C:19]([CH3:21])=[CH2:20])=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].C(O)(=O)C>CO>[CH2:26]([O:25][C:24](=[O:33])[NH:23][C@H:17]([C@H:18]([OH:22])[C:19]([CH3:21])=[CH2:20])[CH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[CH:15][CH:14]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 71562123(S)-Benzyl (1-(4-((tert-butyloxycarbonylamino)methyl)phenyl)-4-methyl-3-oxopent-4-en-2-yl)carbamate

생성물 1

HCID 71562124Benzyl ((2S,3R)-1-(4-((tert-butyloxycarbonylamino)methyl)phenyl)-3-hydroxy-4-methylpent-4-en-2-yl)carbamate

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

Ketone 12 (2.81 g, 4.30 mmol) was dissolved in MeOH (25 mL) and cooled to 0° C. To this were added CeCl3.7H2O (1.5 eq., 6.45 mmol, 2.43 g) and NaBH4 (1.4 eq., 6.0 mmol, 227 mg) portion-wise and the mixture was stirred for 5 minutes. after which TLC analysis indicated a complete conversion. Glacial acetic acid (10 mL) was added and the mixture was concentrated under reduced pressure. The resulting residue was dissolved in EtOAc and extracted with half saturated aq. NaHCO3 (2×) and brine, dried over MgSO4 and concentrated in vacuo. The title compound was obtained as a colourless oil (yield: 1.79 g, 3.94 mmol, 92%). 1H NMR (400 MHz, CDCl3): δ=7.31-7.01 (m, 9H), 5.30 (d, J=9.18 Hz, 1H), 5.06 (s, 1H), 5.00 (d, J=5.19 Hz, 1H), 4.96-4.91 (m, 3H), 4.21 (d, J=4.41 Hz, 1H), 4.16-4.11 (m, 1H), 4.07-3.98 (m, 1H), 2.85 (d, J=12.55 Hz, 1H), 2.65 (dd, J=13.60, 10.41 Hz, 1H), 1.77 (s, 3H), 1.44 (s, 9H) ppm. 13C NMR (100 MHz, CDCl3): δ=155.96, 155.85, 144.44, 137.34, 136.44, 129.34, 128.19, 127.77, 127.66, 127.25, 112.17, 79.25, 76.65, 66.27, 54.06, 44.15, 33.69, 28.22, 18.73 ppm. [α]D23=−18.7 (c=1, CHCl3). HRMS: calcd. for C26H34N2O5 455.25405 [M+H]+. Found 455.25392.

후처리

  1. concentrationthe mixture was concentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in EtOAc
  3. extractionextracted with half saturated aq. NaHCO3 (2×) and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e0da8ecda5904b38b69d184200f251bd
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455431B2

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