Triethylamine → HCID 68549031, compound

HRID 1943308Notes

Reaction equation

HRID 1943308 reaction equation
Br[CH2:2][CH2:3][OH:4].Cl[S:6]([N:9]=[C:10]=[O:11])(=[O:8])=[O:7].[NH2:12][CH:13]([CH2:21][C:22]1[CH:23]=[N:24][C:25]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:26][CH:27]=1)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(N(CC)CC)C>ClCCl>[C:32]([O:31][C:29]([NH:28][C:25]1[N:24]=[CH:23][C:22]([CH2:21][CH:13]([NH:12][S:6]([N:9]2[CH2:2][CH2:3][O:4][C:10]2=[O:11])(=[O:8])=[O:7])[C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])=[CH:27][CH:26]=1)=[O:30])([CH3:35])([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 108982-BromoethanolHCID 70918Chlorosulfonyl isocyanateHCID 68551405HCID 68551405, compound

Product 1

HCID 68549031HCID 68549031, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 0.126 ml of 2-bromoethanol (1.78 mmol, 1.0 equiv.) in dichloromethane (10 ml) was slowly added dropwise to a solution of 251 mg of chlorosulfonyl isocyanate (1.78 mmol, 1.0 equiv.) in dichloromethane (10 ml) under argon at 0° C. in such a way that the temperature did not exceed 10° C. After the addition, the mixture was stirred at 0° C. for a further 30 min. A mixture of 600 mg of tert-butyl 2-amino-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-propionate (1.78 mmol, 1.0 equiv.) and 0.545 ml of triethylamine (3.91 mmol, 2.2 equiv.) in 5 ml of CH2Cl2 was added dropwise to this solution in such a way that the temperature did not rise above 10° C. After the addition, the ice bath was removed and the mixture was stirred at RT for a further 3 h. The residue after concentration was chromatographed on silica gel with heptane/ethyl acetate mixtures as eluent. 320 mg (37% yield) of the title compound were obtained as a colorless solid.

Workup

  1. customdid not exceed 10° C
  2. additionAfter the addition
  3. additionwas added dropwise to this solution in such a way that the temperature
  4. customdid not rise above 10° C
  5. additionAfter the addition
  6. customthe ice bath was removed
  7. stirringthe mixture was stirred at RT for a further 3 h
  8. concentrationThe residue after concentration
  9. customwas chromatographed on silica gel with heptane/ethyl acetate

Sources & evidence

ORD record
ord-2e9cb0e6895c426786ab11cf300b5b4b
Source dataset
uspto-grants-2013_03
Patent number
US08389764B2

Reaction notes

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