Ethyl isocyanate → HCID 131730052, compound

HRID 1875354Notes

Reaction equation

HRID 1875354 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C@H:10]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:12]([CH2:22][OH:23])[CH2:11]2)=[O:8])=[CH:4][CH:3]=1.[CH2:24]([N:26]=[C:27]=[O:28])[CH3:25]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C@H:10]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[C@H:12]([CH2:22][O:23][C:27](=[O:28])[NH:26][CH2:24][CH3:25])[CH2:11]2)=[O:8])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanate2×HCID 58748309HCID 58748309, compound

Product 1

HCID 131730052HCID 131730052, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

120.0 mg (0.3 mmol) tert. Butyl (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-2-hydroxymethyl-pyrrolidine-1-carboxylate are refluxed in 5 ml of toluene with 30 μl (0.38 mmol) ethylisocyanate for three hours. Then 100 μl ethyl isocyanate are added three times at three hour intervals and the mixture is refluxed for a further 16 hours. Then the mixture is cooled, evaporated to dryness and purified by flash chromatography on silica gel (eluant DCM/methanol 100:3).

Workup

  1. temperaturethe mixture is refluxed for a further 16 hours
  2. temperatureThen the mixture is cooled
  3. customevaporated to dryness
  4. custompurified by flash chromatography on silica gel (eluant DCM/methanol 100:3)

Sources & evidence

ORD record
ord-abb2235814d74f06beb7bd665ea4e5cd
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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