Acetic Acid → 17beta-[(2-(4-Aminosulfonylphenyl)ethyl)amino)-5alpha-androstane Hemihydrate

HRID 327933

Reaction equation

HRID 327933 reaction equation
[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]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1019275alpha-Androstan-17-oneHCID 1696824-(2-Aminoethyl)benzenesulfonamideHCID 5003444Sodium cyanoborohydride2×

Product 1

HCID 8846159917beta-[(2-(4-Aminosulfonylphenyl)ethyl)amino)-5alpha-androstane Hemihydrate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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-H2O giving 0.76 g of the title compound

Sources & evidence

ORD record
ord-cece004ada9547c0942b1d538339e708
Source dataset
uspto-grants-1993_12
Patent number
US05274089

Linked notes

Loading…