4-Methylmorpholine → isobutyl N-[9-(3,17beta-dihydroxyoestra-1,3,5(10)-trien-7alpha-yl)nonyl]-N-methylcarbamoate

HRID 543018Notes

Reaction equation

HRID 543018 reaction equation
CN1CCOCC1.Cl[C:9]([O:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:10].[CH3:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C@@H:27]1[CH2:44][C:43]2[CH:42]=[C:41]([OH:45])[CH:40]=[CH:39][C:38]=2[C@@H:37]2[C@@H:28]1[C@H:29]1[C@@:33]([CH2:35][CH2:36]2)([CH3:34])[C@@H:32]([OH:46])[CH2:31][CH2:30]1.C(=O)(O)[O-].[Na+]>O1CCCC1>[OH:45][C:41]1[CH:40]=[CH:39][C:38]2[C@@H:37]3[C@H:28]([C@H:29]4[C@@:33]([CH2:35][CH2:36]3)([CH3:34])[C@@H:32]([OH:46])[CH2:31][CH2:30]4)[C@H:27]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH3:16])[C:9](=[O:10])[O:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:44][C:43]=2[CH:42]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 543355367alpha-(9-Methylaminononyl)oestra-1,3,5(10)-triene-3,17beta-diol

Product 1

HCID 70447132isobutyl N-[9-(3,17beta-dihydroxyoestra-1,3,5(10)-trien-7alpha-yl)nonyl]-N-methylcarbamoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Methylmorpholine (0.028 ml.) and isobutyl chloroformate (0.038 ml.) were successively added to a stirred solution of 7α-(9-methylaminononyl)oestra-1,3,5(10)-trien-3,17β-diol (Example 28; 0.08 g.) in tetrahydrofuran (3 ml.) and the mixture was stirred at laboratory temperature for 150 minutes. Saturated aqueous sodium bicarbonate solution (2 ml.) was added and the mixture was extracted three times with methylene chloride (10 ml. each time). The combined extracts were washed with water (5 ml.), dried and evaporated to dryness and there was thus obtained as residual oil isobutyl N-[9-(3,17β-dihydroxyoestra-1,3,5(10)-trien-7α-yl)nonyl]-N-methylcarbamoate.

Workup

  1. extractionthe mixture was extracted three times with methylene chloride (10 ml
  2. washThe combined extracts were washed with water (5 ml.)
  3. customdried
  4. customevaporated to dryness and there

Sources & evidence

ORD record
ord-3b9b5f4e451c4dc8a22c6f2d88fc1100
Source dataset
uspto-grants-1987_04
Patent number
US04659516

Reaction notes

Loading…