Acetic Acid → N-[(2S)-2-(tert-butoxycarbonylamino)-3-(phenylmethoxy)propyl]-N-[2-(tert-butoxycarbonylamino)-3-(phenylmethoxy)Propyl]amine

HRID 1094680노트

반응식

HRID 1094680 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:10][NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:21]([O:25][C:26]([NH:28][C@@H:29]([CH2:32][O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH:30]=O)=[O:27])([CH3:24])([CH3:23])[CH3:22].C([BH3-])#N.[Na+].C(O)(=O)C>C(O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:12][O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:10][NH:11][CH2:30][CH:29]([NH:28][C:26]([O:25][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:27])[CH2:32][O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 11196731(S)-tert-butyl 3-(benzyloxy)-1-oxopropan-2-ylcarbamateHCID 60204732N2-Boc-(S)-3-(benzyloxy)propane-1,2-diamine

생성물 1

HCID 66639988N-[(2S)-2-(tert-butoxycarbonylamino)-3-(phenylmethoxy)propyl]-N-[2-(tert-butoxycarbonylamino)-3-(phenylmethoxy)Propyl]amine수율 22.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

The product from Example 17B (0.35 g, 1.25 mmol) and the product from Example 17A (0.36 g, 1.29 mmol) in absolute ethanol (12 mL) were treated with sodium cyanoborohydride (94 mg, 1.50 mmol) and a catalytic amount of acetic acid. The resulting mixture was stirred at ambient temperature overnight. The mixture was partitioned between water (40 mL) and ethyl acetate (3×40 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel (hexanes:ethyl acetate, 1:1) to provide the title compound (0.15 g, 22%).

후처리

  1. customThe mixture was partitioned between water (40 mL) and ethyl acetate (3×40 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-65b73a50f9144cba82a11cfea3860823
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133892B2

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