tert-Butanol → HCID 66755636, compound

HRID 1642057Notes

Reaction equation

HRID 1642057 reaction equation
[C:1](O)([CH3:4])([CH3:3])[CH3:2].Cl[S:7]([N:10]=C=O)(=[O:9])=[O:8].[CH2:13]([O:15][C:16](=[O:28])[CH2:17][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=1)[CH3:14].C(N(CC)CC)C>C(Cl)Cl>[CH2:13]([O:15][C:16](=[O:28])[CH2:17][N:18]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=1)[S:7]([NH:10][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:9])=[O:8])[CH3:14]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 19172Glycine, N-(m-nitrophenyl)-, ethyl esterHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 66755636HCID 66755636, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a mixture of 25.7 mmol tert.butanol and 20 ml of CH2Cl2 are added 10.3 mmol of ClSO2NCO and the mixture obtained is stirred at rt for 45 minutes. The mixture obtained is slowly added to a solution of 5.14 mmol of (3-nitro-phenylamino)-acetic acid ethyl ester and 15.4 mmol of triethylamine in 50 ml of CH2Cl2 at 0° and the mixture obtained is stirred at 0° for 2.5 hours. The mixture obtained is diluted with CH2Cl2 and the dilution is extracted with HCl (0.1N). The organic layer obtained is dried, and solvent is evaporated. (3-Nitro-phenyl-N-(t-butylaminosulfonyl)amino)-acetic acid ethyl ester is obtained.

Workup

  1. customthe mixture obtained
  2. customThe mixture obtained
  3. customthe mixture obtained
  4. stirringis stirred at 0° for 2.5 hours
  5. customThe mixture obtained
  6. extractionthe dilution is extracted with HCl (0.1N)
  7. customThe organic layer obtained
  8. customis dried
  9. customsolvent is evaporated

Sources & evidence

ORD record
ord-e705af964c8d48d386d41d1f841df854
Source dataset
uspto-grants-2012_02
Patent number
US08119617B2

Reaction notes

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