Water → HCID 87553220, compound

HRID 1182870Notes

Reaction equation

HRID 1182870 reaction equation
C(O)(=O)/C=C/C(O)=O.[NH2:9][CH2:10][CH2:11][O:12]/[N:13]=[C:14]1/[C:15]([CH3:35])([CH3:34])[C:16]2[C@:29]([CH3:32])([CH2:30][CH2:31]/1)[C@@H:28]1[C@H:19]([C@H:20]3[C@@:24]([CH2:26][CH2:27]1)([CH3:25])[C@@H:23]([OH:33])[CH2:22][CH2:21]3)[CH2:18][CH:17]=2.CCN(CC)CC.[CH:43]1[C:55]2[CH:54]([CH2:56][O:57][C:58](Cl)=[O:59])[C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:47]=2[CH:46]=[CH:45][CH:44]=1.O>C(Cl)Cl>[CH:43]1[C:55]2[CH:54]([CH2:56][O:57][C:58]([NH:9][CH2:10][CH2:11][O:12]/[N:13]=[C:14]3/[C:15]([CH3:35])([CH3:34])[C:16]4[C@:29]([CH3:32])([CH2:30][CH2:31]/3)[C@@H:28]3[C@H:19]([C@H:20]5[C@@:24]([CH2:26][CH2:27]3)([CH3:25])[C@@H:23]([OH:33])[CH2:22][CH2:21]5)[CH2:18][CH:17]=4)=[O:59])[C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:47]=2[CH:46]=[CH:45][CH:44]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 343679-Fluorenylmethyl chloroformateHCID 87573867HCID 87573867, compound

Product 1

HCID 87553220HCID 87553220, compoundYield 128.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of a mixture of (E)-3-(2-aminoethoxyimino)-4,4-dimethylandrost-5-en-17β-ol (Example 2, 250 mg) and Et3N (0.14 ml) under N2 in DCM (10 ml) at 0° C., 9-fluorenylmethoxycarbonyl chloride (170 mg) was added. After stirring at RT for 15 minutes, water was added and the mixture was extracted with DCM. The organic phase was washed with 5% NaHCO3 dried over Na2SO4 and evaporated to dryness to give 3-(E)-{2-[N-(9-fluorenylmethoxy-carbonyl)]aminoethoxyimino}-4,4-dimethylandrost-5-en-17β-ol (392 mg, 99%).

Workup

  1. extractionthe mixture was extracted with DCM
  2. washThe organic phase was washed with 5% NaHCO3
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-31f322d61feb40c28d03a92798f79550
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

Loading…