Methanol → Methyl (3S)-4-{[(1,1-dimethylethyl)(diphenyl)silyl]oxy}-3-({[(phenylmethyl)oxy]carbonyl}amino)butanoate

HRID 1094749

반응식

HRID 1094749 반응식
[CH3:1]CN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CO.[CH3:34][C:35]([Si:38]([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[O:39][CH2:40][C@@H:41]([NH:46][C:47]([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:48])[CH2:42][C:43]([OH:45])=[O:44])([CH3:37])[CH3:36]>CN(C=O)C.[Cl-].[Na+].O>[CH3:37][C:35]([Si:38]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[O:39][CH2:40][C@@H:41]([NH:46][C:47]([O:49][CH2:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)=[O:48])[CH2:42][C:43]([O:45][CH3:1])=[O:44])([CH3:34])[CH3:36]

참가 물질

7

반응물 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 60109761(3S)-4-{[(1,1-Dimethylethyl)(diphenyl)silyl]oxy}-3-({[(phenylmethyl)oxy]carbonyl}amino)butanoic acid

생성물 1

HCID 59396013Methyl (3S)-4-{[(1,1-dimethylethyl)(diphenyl)silyl]oxy}-3-({[(phenylmethyl)oxy]carbonyl}amino)butanoate수율 90.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

In a 1000 ml round-bottomed flask (3S)-4-{[(1,1-dimethylethyl)(diphenyl)silyl]oxy}-3-({[(phenylmethyl)oxy]carbonyl}amino)butanoic acid D2 (15 g) was dissolved in DMF (200 ml). To this solution DIPEA (28.8 ml, 165 mmol) and TBTU (11.46 g, 35.7 mmol) were added and the solution left under stirring at room temperature for 20 minutes. After this time to the brown solution MeOH (11 ml) was added and the mixture left under stirring at room temperature for 30 minutes. The reaction mixture was transferred into a separatory funnel containing brine (600 ml) and extracted with EtOAc (5×200 ml). The organic phases were washed with water (3×100 ml), dried (Na2SO4) and evaporated under vacuum to give an orange oil. This material was purified by column chromatography on silica gel (flash master, Cy/EtOAc from 100/0 to 80/20) to give the title compound D3 (13.9 g) as a yellow solid. MS: (ES/+) m/z: 506 (M+1). C29H35NO5Si requires 505. 1H NMR (400 MHz, CDCl3-d6) δ (ppm): 7.69-7.29 (m, 15 H), 5.4-5.26 (m, 1 H), 5.11 (m, 2 H), 4.25-4.14 (m, 1 H), 3.82-3.68 (m, 2H), 3.64 (s, 3 H), 2.79-2.52 (m, 2 H), 1.08 (s, 9 H).

후처리

  1. waitthe solution left
  2. waitthe mixture left
  3. stirringunder stirring at room temperature for 30 minutes
  4. customThe reaction mixture was transferred into a separatory funnel
  5. extractionextracted with EtOAc (5×200 ml)
  6. washThe organic phases were washed with water (3×100 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated under vacuum
  9. customto give an orange oil
  10. customThis material was purified by column chromatography on silica gel (flash master, Cy/EtOAc from 100/0 to 80/20)

출처 및 근거

ORD 기록
ord-76a39f9b6ce0420d8097d8ef7d2c1c9b
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133908B2

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