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Methanol → tert-butyl (2S,4S)-4-(benzyloxymethyl)-1-hydroxy-5-methylhexan-2-ylcarbamate

HRID 507836
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HRID 507836 반응식
[CH2:1]([O:8][CH2:9][C@H:10]([CH:26]([CH3:28])[CH3:27])[CH2:11][C@H:12]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13]C(OC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].C[OH:32]>O1CCCC1>[CH2:1]([O:8][CH2:9][C@H:10]([CH:26]([CH3:28])[CH3:27])[CH2:11][C@H:12]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:13][OH:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

5

반응물 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 68623312methyl 4(S)-benzyloxymethyl-2(S)-tert-butoxycarbonylamino-5-methylhexanecarboxylate

생성물 1

HCID 70642503tert-butyl (2S,4S)-4-(benzyloxymethyl)-1-hydroxy-5-methylhexan-2-ylcarbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The stirred solution of 5.0 g of methyl 4(S)-benzyloxymethyl-2(S)-tert-butoxycarbonylamino-5-methylhexanecarboxylate [CAS 180182-92-7] in 80 ml of tetrahydrofuran is admixed in portions with 0.660 g of lithium borohydride. The reaction mixture is stirred for another 3 hours, admixed cautiously with 25 ml of methanol and concentrated by evaporation at 40° C. The residue is dissolved once more in 70 ml of methanol and again concentrated by evaporation at 40° C. The residue is admixed with 1M HCl (cold) and extracted with dichloromethane (3×). The combined organic phases are washed with water, dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a colourless oil. Rf=0.32 (1:1 EtOAc-heptane); Rt=4.86 (gradient I).

후처리

  1. concentrationconcentrated by evaporation at 40° C
  2. dissolutionThe residue is dissolved once more in 70 ml of methanol
  3. concentrationagain concentrated by evaporation at 40° C
  4. extractionextracted with dichloromethane (3×)
  5. washThe combined organic phases are washed with water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-e034e51d4304480183ff755b96f9a76d
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07786307B2

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