Ethyl isocyanate → HCID 86752673, compound

HRID 1292393Notes

Reaction equation

HRID 1292393 reaction equation
[CH2:1]([O:8][C:9](=[O:49])[N:10]([CH2:31][CH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:37][CH:36]=1)[CH2:11][CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=2)[NH:15][C:14]=1[C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:50]([N:52]=[C:53]=[O:54])[CH3:51]>>[CH2:1]([O:8][C:9]([N:10]([CH2:31][CH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)=[CH:37][CH:36]=1)[CH2:11][CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:22][C:53](=[O:54])[NH:52][CH2:50][CH3:51])[CH:20]=2)[NH:15][C:14]=1[C:23]1[CH:24]=[C:25]([CH3:30])[CH:26]=[C:27]([CH3:29])[CH:28]=1)=[O:49])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8022Ethyl isocyanate2×HCID 70227002HCID 70227002, compound

Product 1

HCID 86752673HCID 86752673, compound

Procedure

To a solution of [4-(4-benzyloxyphenyl)-butyl]-[2-[2-(3,5-dimethylphenyl)-5-hydroxy-1H-indol-3-yl]ethyl]carbamic acid benzyl ester (50 mg in 0.5 mL dry tetrahydrofuran) was added 0.035 mL of ethyl isocyanate and the mixture stirred at room temperature. Over the course of 2 weeks, additional ethyl isocyanate was added in portions and the mixture heated to reflux for several days after which time it was cooled to room temperature, concentrated in vacuo and purified by flash chromatography on silica gel (hexane:ethyl acetate, 2:1) to give the title compound (20 mg).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for several days after which time it
  3. temperaturewas cooled to room temperature
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography on silica gel (hexane:ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-53290def764c41fcaab29989505d1493
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

Loading…