Tetrahydrofuran → HCID 178484174、化合物

HRID 1254353ノート

反応式

HRID 1254353 の反応式
O[C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][C@H:9]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:10][N:11]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH3:12])[CH2:4][CH2:3]1.CCN(CC)CC.[F:38]C(F)(S(F)(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.C1COCC1>>[F:38][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][C@H:9]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:10][N:11]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH3:12])[CH2:4][CH2:3]1

参加物

5

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 178484178HCID 178484178、化合物

生成物 1

HCID 178484174HCID 178484174、化合物収率 40%

実験手順

A mixture of tert-butyl (S)-1-(trans-4-hydroxycyclohexyl)-3-(N-(benzyloxycarbonyl)-N-methylamino)propan-2-ylcarbamate (3 g, 7 mmol), Et3N (12 mL, 88 mmol), NEt3(HF)3 (4.71 mL, 29 mmol) and perfluorobutanesulfonyl fluoride (5.21 mL, 29 mmol) was stirred in THF (70 mL, 1 mmol/10 mL) at 50° C. until HPLC revealed complete conversion. The reaction mixture was quenched with water and extracted with EtOAc (2×100 mL), dried over MgSO4 and evaporated. The residue was then purified by prep HPLC to give tert-butyl (S)-1-(trans-4-fluorocyclohexyl)-3-(N-(benzyloxycarbonyl)-N-methylamino)propan-2-ylcarbamate (1.16 g, 40%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 1.41(d, 9 H), 1.68(m, 6 H), 1.96(m, 3 H), 2.98(d, 3 H), 3.20(m, 1 H), 3.52(m, 1 H), 3.90(m, 1 H), 5.13(d, 2 H), 7.33(m, 5 H).

後処理

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc (2×100 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was then purified by prep HPLC

出典と根拠

ORDレコード
ord-d41dc7efd4384ecd8ef74d8905b5815d
出典データセット
uspto-grants-2013_06
特許番号
US08455521B2

反応ノート

読み込み中…