Hydrochloric Acid → Carbamic acid, (6-hydroxyhexyl)-, phenylmethyl ester

HRID 322488

반응식

HRID 322488 반응식
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13](=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].CO.Cl>C1COCC1>[CH2:23]([O:22][C:20](=[O:21])[NH:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][OH:12])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21225700DiisobutylaluminumhydrideHCID 43404641Methyl 6-(benzyloxycarbonylamino)hexanoate

생성물 1

HCID 4184071Carbamic acid, (6-hydroxyhexyl)-, phenylmethyl ester수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of diisobutylaluminum hydride (49 mL, 1.5 M in toluene) in THF (150 mL) cooled to −78° C. was added a solution of 6-benzyloxycarbonylamino-hexanoic acid methyl ester (10 g, 37 mmol) in THF (100 mL) . The reaction mixture was stirred for 4 h and methanol (2.5 mL) was added carefully at −78 to −75° C. After 2 h, the mixture was poured to 250 mL of 1 N HCl solution cooled in ice-bath, extracted with ethyl acetate (300 mL), washed with brine (3×100 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography (silica, 50% ethyl acetate in hexane) to yield the titled compound (7.1 g, 80%); white solid, mp 67-68° C.

후처리

  1. waitAfter 2 h
  2. temperaturecooled in ice-bath
  3. extractionextracted with ethyl acetate (300 mL)
  4. washwashed with brine (3×100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography (silica, 50% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-91e6c33f70854a7cbe1e39ff64ca13f9
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211241B1

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