Acetic Acid → HCID 59997204, 화합물

HRID 1253979노트

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HRID 1253979 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([N:13]([CH2:38][CH:39]([CH3:41])[CH3:40])[CH2:14][C@@H:15]([OH:37])[C@@H:16]([NH:25][C:26](=[O:36])[O:27][C@@H:28]3[C@H:35]4[C@H:31]([O:32][CH2:33][CH2:34]4)[O:30][CH2:29]3)[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)(=[O:12])=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1.[H-].[Na+].[CH3:44][NH:45][C:46](=[O:49])[CH2:47]Br.C(O)(=O)C>O1CCCC1.C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([N:13]([CH2:38][CH:39]([CH3:41])[CH3:40])[CH2:14][C@@H:15]([OH:37])[C@@H:16]([NH:25][C:26](=[O:36])[O:27][C@@H:28]3[C@H:35]4[C@H:31]([O:32][CH2:33][CH2:34]4)[O:30][CH2:29]3)[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:47][C:46]([NH:45][CH3:44])=[O:49])=[CH:20][CH:19]=3)(=[O:12])=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 24758Sodium hydride2회HCID 154907452-Bromo-N-methylacetamideHCID 59997191(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl) (isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate

생성물 1

HCID 59997204HCID 59997204, 화합물수율 15.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate (60 mg, 0.1 mmol) in anhydrous tetrahydrofuran (1.5 mL) was added 60% sodium hydride/mineral oil dispersion (4 mg, 0.1 mmol). The mixture was stirred for 10 min at ambient temperature under nitrogen atmosphere and a solution of N-methyl-2-bromoacetamide (17 mg, 0.11 mmol) in anhydrous tetrahydrofuran (0.5 mL) was added. After 2 h, an additional portion of 60% sodium hydride/mineral oil dispersion (4 mg, 0.1 mmol) was added. After 15 min, acetic acid (0.1 mL) was added and the mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate/water, dried (sodium sulfate), evaporated, and purified by chromatography (silica gel, ethyl acetate) to provide the title compound as a white solid (10 mg). 1H NMR (DMSO-d6): δ 0.78 (3H, d), 0.82 (3H, d) 1.15-1.22 9 (1H, m), 1.2 (1H, quintuplet), 1.9-2.0 (1H, m), 2.35 (1H, t), 2.6 (3H, d), 2.65-2.80 (3H, m), 2.9 (1H, d), 2.95 (1H, dd), 3.2-3.3 (1H, m), 3.4-3.5 (1H, m) 3.5-3.6 (3H, m), 3.7 (1H, t), 3.8 (1H, dd), 4.4 (2H, s), 4.8 (1H, dt), 5.0 (1H, d), 5.5 (1H, d), 6.2 (2H, s), 6.8 (2H, d), 7.0-7.2 (3H, m), 7.22 (1H, s), 7.25 (1H, d), 7.3 (1H, d), 8.0 (1H; br s); MS: 664 (MH+);

후처리

  1. waitAfter 2 h
  2. waitAfter 15 min
  3. washwashed with saturated sodium bicarbonate/water
  4. dry with materialdried (sodium sulfate)
  5. customevaporated
  6. custompurified by chromatography (silica gel, ethyl acetate)

출처 및 근거

ORD 기록
ord-989a35a07de2423c86defc0c89c9d096
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455497B2

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