Thiourea → HCID 89668491, compound

HRID 1482302Notes

Reaction equation

HRID 1482302 reaction equation
NC(N)=[S:3].[C:5]([O:9][C:10](=[O:24])[C@@H:11]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH:13]1[CH2:15]O1)([CH3:8])([CH3:7])[CH3:6]>CO>[C:5]([O:9][C:10](=[O:24])[C@@H:11]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][CH:13]1[CH2:15][S:3]1)([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 89668476HCID 89668476, compound2×

Product 1

HCID 89668491HCID 89668491, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol (4 ml) and thiourea (83 mg, 1.096 mmol) were added to (S)-2-tert-butoxycarbonylamino-3-oxiranyl-propionic acid tert-butyl ester (Compound 30) (315 mg, 1.096 mmol), and the reaction solution was heated at reflux for 1.5 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by normal-phase silica gel column chromatography (hexane/ethyl acetate) to afford (S)-2-tert-butoxycarbonylamino-3-thiiranyl-propionic acid tert-butyl ester (Compound 31) (278 mg, 84%).

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureat reflux for 1.5 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customthe resulting residue was purified by normal-phase silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-dcb2dda3a800419ea669b315a31bcc8f
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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