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Hydrogen Peroxide → ditert-butyl(1S,2S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate

HRID 2173005
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HRID 2173005 반응식
C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[C:15]([O:19][C:20]([NH:22][C@@:23]1([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:28][C:27](=[O:29])[C@@H:26]2[C@H:24]1[C@H:25]2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:21])([CH3:18])([CH3:17])[CH3:16].C([O-])([O-])=O.[Na+].[Na+].OO>O1CCCC1.O>[C:15]([O:19][C:20]([NH:22][C@@:23]1([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:28][C@H:27]([OH:29])[C@@H:26]2[C@H:24]1[C@H:25]2[C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])=[O:21])([CH3:18])([CH3:16])[CH3:17]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 3611392Lithium tri-s-butylborohydrideHCID 59712878Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-oxo-, 2,6-bis(1,1-dimethylethyl) ester, (1S,2S,5R,6R)-

생성물 1

HCID 59712892ditert-butyl(1S,2S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate
수율 86.1%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

Add 1M lithium tri(sec-butyl)borohydride in tetrahydrofuran (2.67 L, 2.67 mol) dropwise to a solution of di-tert-butyl(1S,2S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate (1000 g, 2.43 mol) in dry tetrahydrofuran (10 L) at 0° C. under nitrogen. After 2 hours at 0° C., 2M Na2CO3 in water (850 g, 8.02 mol) is added at 0° C. over 2 hours followed by 35% aqueous hydrogen peroxide (740 mL, 8.99 mol) in water (3.3 L). After 40 minutes, the mixture is warmed to ambient temperature whereupon the organic phase is separated. The organic phase is diluted with methyl tert-butyl ether (3.5 L) and the layers are separated again. The aqueous phase is extracted with methyl tert-butyl ether (3.5 L). All the combined organic phases are washed successively with 1M aqueous Na2SO3 (2.67 L), water (2.67 L), and brine (2.67 L), dried over sodium sulfate, filtered and concentrated to a volume of 3 L. The precipitated solid is filtered and washed with heptane (1.3 L) to obtain the title compound (864.76 g). The mother liquors are concentrated to dryness and the residue is triturated with heptane (500 mL) and filtered to obtain additional title compound (130.64 g, total 995.4 g, yield 99%). MS (m/z): 436 (M+23).

후처리

  1. waitAfter 40 minutes
  2. customis separated
  3. additionThe organic phase is diluted with methyl tert-butyl ether (3.5 L)
  4. customthe layers are separated again
  5. extractionThe aqueous phase is extracted with methyl tert-butyl ether (3.5 L)
  6. washAll the combined organic phases are washed successively with 1M aqueous Na2SO3 (2.67 L), water (2.67 L), and brine (2.67 L)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to a volume of 3 L
  10. filtrationThe precipitated solid is filtered
  11. washwashed with heptane (1.3 L)

출처 및 근거

ORD 기록
ord-2b66347230aa4ba981b33a6e74dc98be
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09056844B2

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