醋酸 → HCID 88461599，化合物

HRID 1885797

反应方程式

HRID 1885797 反应方程式
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.C(O)(=O)C.[CH3:18][C@:19]12[CH2:36][CH2:35][C@H:34]3[C@@H:24]([CH2:25][CH2:26][C@@H:27]4[C@:32]3([CH3:33])[CH2:31][CH2:30][CH2:29][CH2:28]4)[C@@H:23]1[CH2:22][CH2:21][C:20]2=O.C([BH3-])#N.[Na+]>CO.C1COCC1>[OH2:11].[NH2:13][S:10]([C:7]1[CH:6]=[CH:5][C:4]([CH2:3][CH2:2][NH:1][C@H:20]2[CH2:21][CH2:22][C@H:23]3[C@H:24]4[C@H:34]([CH2:35][CH2:36][C@:19]23[CH3:18])[C@:32]2([CH3:33])[C@H:27]([CH2:28][CH2:29][CH2:30][CH2:31]2)[CH2:26][CH2:25]4)=[CH:9][CH:8]=1)(=[O:11])=[O:12].[NH2:13][S:10]([C:7]1[CH:6]=[CH:5][C:4]([CH2:3][CH2:2][NH:1][C@H:20]2[CH2:21][CH2:22][C@H:23]3[C@H:24]4[C@H:34]([CH2:35][CH2:36][C@:19]23[CH3:18])[C@:32]2([CH3:33])[C@H:27]([CH2:28][CH2:29][CH2:30][CH2:31]2)[CH2:26][CH2:25]4)=[CH:9][CH:8]=1)(=[O:11])=[O:12]

参与物

7

反应物 4

HCID 176醋酸HCID 1019275alpha-Androstan-17-oneHCID 1696824-(2-氨乙基)苯磺酰胺HCID 5003444氰基硼氢化钠2 次

产物 1

HCID 88461599HCID 88461599，化合物

试剂、催化剂与溶剂 2

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂HCID 8028四氢呋喃溶剂

实验过程

A solution of 3.39 g of 4-(2-aminoethyl)benzenesulfonamide in 50 ml of MeOH and 150 ml of THF was acidified with 3 ml (3.15 g) of acetic acid. Then 2.32 g of 5α-androstan-17-one was added. After a solution was obtained, 1.2 g of sodium cyanoborohydride was added. The resulting solution was stirred for 5 hours. An additional 1.2 g of sodium cyanoborohydride was added. The stirring was continued for 19 hours. The solvent was evaporated from the solution. The residue was treated with 200 ml of water, made basic with 50% NaOH solution, and extracted with CH2Cl2 (3×100 ml). The combined extracts were washed with 50 ml of brine and dried over MgSO4. Evaporation of the solvent left 3.75 g of solid. The solid was chromatographed on a 400 g column of silica gel. The column was eluted with 10% MeOH--CH2Cl2 and 100 ml fractions were collected. The fractions were assayed by silica gel TLC (1×4") (10% MeOH--CH2Cl2). Fractions 18-30 were combined and crystallized from MeOH--H2O giving 0.76 g of the title compound.

后处理

  1. customAfter a solution was obtained
  2. waitThe stirring was continued for 19 hours
  3. customThe solvent was evaporated from the solution
  4. additionThe residue was treated with 200 ml of water
  5. extractionextracted with CH2Cl2 (3×100 ml)
  6. washThe combined extracts were washed with 50 ml of brine
  7. dry with materialdried over MgSO4
  8. customEvaporation of the solvent
  9. waitleft 3.75 g of solid
  10. customThe solid was chromatographed on a 400 g column of silica gel
  11. washThe column was eluted with 10% MeOH
  12. customCH2Cl2 and 100 ml fractions were collected
  13. customcrystallized from MeOH

来源与证据

ORD记录
ord-b448fd2987d14283b33bf5e1e74c7085
来源数据集
uspto-grants-1992_09
专利号
US05145874

关联笔记

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