Triethylamine → HCID 57947757, 화합물

HRID 416333노트

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HRID 416333 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:10][OH:11])[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[O:7])([CH3:2])([CH3:4])[CH3:3]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 11288857350832-82-5

생성물 1

HCID 57947757HCID 57947757, 화합물수율 90%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of (S)-2-(tert-butoxycarbonylamino)-6-methoxy-6-oxohexanoic acid (23.5 g, 85 mmol) in anhydrous THF (100 mL) was added Et3N (14.2 mL, 102 mmol, 1.2 equiv.). The solution was cooled down to 0° C. and isobutyl chloroformate (12.2 mL, 93.5 mmol, 1.1 equiv.) was added dropwise. The solution was stirred for 30 min. The precipitate was filtered off. The filtrate was cooled down to 0° C. and a suspension of sodium borohydride (6.5 g, 170 mmol, 2 equiv.) in H2O (3 mL) was added in one portion. The reaction was stirred for 1 h, and quenched with saturated NH4Cl. THF was removed. The residue was dissolved into EtOAc (400 mL) and extracted with saturated NH4Cl twice. The organic layers were combined, dried and concentrated. The residue was purified on silica gel column (hexanes/EtOAc 1:1) to give (S)-methyl 5-(tert-butoxycarbonylamino)-6-hydroxyhexanoate (20 g, 90%) as a colorless oil. LRMS (M-Boc+H+) m/z 162.1.

후처리

  1. filtrationThe precipitate was filtered off
  2. temperatureThe filtrate was cooled down to 0° C.
  3. additionwas added in one portion
  4. stirringThe reaction was stirred for 1 h
  5. customquenched with saturated NH4Cl
  6. customTHF was removed
  7. dissolutionThe residue was dissolved into EtOAc (400 mL)
  8. extractionextracted with saturated NH4Cl twice
  9. customdried
  10. concentrationconcentrated
  11. customThe residue was purified on silica gel column (hexanes/EtOAc 1:1)

출처 및 근거

ORD 기록
ord-1a8703c52bfa41c9887b9c6ed0deb96a
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088793B2

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