Triethylamine → HCID 53671572, compound

HRID 726142Notes

Reaction equation

HRID 726142 reaction equation
O[CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C:12](=[CH:13][C:14](=[O:22])[CH2:15][CH2:16]1)[N:11]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:10]3.C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:42]=[N+:43]=[N-:44].[Na+]>ClCCl.CN(C1C=CN=CC=1)C.CN(C)C=O.C(OCC)(=O)C>[N:42]([CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C:12](=[CH:13][C:14](=[O:22])[CH2:15][CH2:16]1)[N:11]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:10]3)=[N+:43]=[N-:44]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 53807267HCID 53807267, compound

Product 1

HCID 53671572HCID 53671572, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 17β-hydroxymethyl-6-t-butoxycarbonyl-6-azaandrost-4-en-3-one (2.03 g, 5.04 mmol) prepared in example 3, part 15, in dichloromethane (50 mL) is treated with triethylamine (0.88 mL, 6.3 mmol), DMAP (0.155 g, 1.27 mmol) and methanesulfonyl chloride (0.43 mL, 5.6 mmol). After 3 hrs, the reaction is diluted with dichloromethane (50 mL), washed with 1N HCl, saturated aqueous NaCl and dried over MgSO4. Concentration gives a white foam which is dissolved in dimethylformamide (50 mL), treated with sodium azide (0.94 g, 14.5 mmol) and heated to 75° C. for 16 hrs. The reaction is poured into ethyl acetate, washed with water (5×100 mL), dried over MgSO4, concentrated and chromatographed on silica gel (20% ethyl acetate/hexane) to give 17β-azidomethyl-6-t-butoxycarbonyl-6-azaandrost-4-en-3-one as a white foam of sufficient purity to carry on to the next step.

Workup

  1. washwashed with 1N HCl, saturated aqueous NaCl
  2. dry with materialdried over MgSO4
  3. concentrationConcentration
  4. customgives a white foam which
  5. washwashed with water (5×100 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customchromatographed on silica gel (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5139abe8995842e0aeb286d04114b3eb
Source dataset
uspto-grants-1998_01
Patent number
US05708001

Reaction notes

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