1,2-Dichloroethane → HCID 59511757, compound

HRID 1157451Notes

Reaction equation

HRID 1157451 reaction equation
Cl.[NH2:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C@@H:14]([CH3:17])[CH2:15][OH:16])=[CH:8][C:4]=1[C:5]([OH:7])=O.[NH2:18][CH2:19][C:20]([NH:22][CH:23]([CH3:25])[CH3:24])=[O:21].C(N(CC)CC)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[NH2:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C@@H:14]([CH3:17])[CH2:15][OH:16])=[CH:8][C:4]=1[C:5]([NH:18][CH2:19][C:20](=[O:21])[NH:22][CH:23]([CH3:25])[CH3:24])=[O:7]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 5338492-Amino-N-isopropylacetamideHCID 68524390HCID 68524390, compound

Product 1

HCID 59511757HCID 59511757, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-5-[(S)-(+)-3-hydroxy-2-methylpropoxy]benzoic acid hydrochloride (200 mg, 0.76 mmol), 2-amino-N-isopropylacetamide*HCl (INTERMEDIATE I.1) (105 mg, 0.70 mmol) and triethylamine (0.23 mL, 1.68 mmol) in DMF (5 mL) was stirred at room temperature for 5 min. EDC (176 mg, 0.92 mmol) and HOBt (124 mg, 0.92 mmol) were added and stirring continued at room temperature for 16 h. The mixture was partitioned between ethyl acetate and sat. NaHCO3 (aq.) and the aqueous extracted with additional ethyl acetate. The combined organics were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude 2-amino-5-[(S)-(+)-3-hydroxy-2-methylpropoxy]-N-(isopropylcarbamoylmethyl)benzamide (INTERMEDIATE VIII.1) was used directly in the next reaction.

Workup

  1. stirringstirring
  2. waitcontinued at room temperature for 16 h
  3. customThe mixture was partitioned between ethyl acetate and sat. NaHCO3 (aq.)
  4. extractionthe aqueous extracted with additional ethyl acetate
  5. washThe combined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude 2-amino-5-[(S)-(+)-3-hydroxy-2-methylpropoxy]-N-(isopropylcarbamoylmethyl)benzamide (INTERMEDIATE VIII.1) was used directly in the next reaction

Sources & evidence

ORD record
ord-349a2737e5714664a84460541d331871
Source dataset
uspto-grants-2010_10
Patent number
US07807686B2

Reaction notes

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