HCID 69192005, compound → HCID 69191919, compound

HRID 1057506Notes

Reaction equation

HRID 1057506 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([N:16]1[CH2:22][C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[CH:19]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:18][CH2:17]1)=[O:15])=O)(C)(C)C>Cl.C(OCC)(=O)C>[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([N:16]1[CH2:22][C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[CH:19]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:18][CH2:17]1)=[O:15]

Participants

4

Reactant 1

HCID 69192005HCID 69192005, compound

Product 1

HCID 69191919HCID 69191919, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2-(2-(N-(4-tertbutoxycarbonylaminobut-1-yl) carbamoyl)-1H,3H,4H-5H-benzo[e]azapin-5-yl)acetate was stirred in HCl in ethyl acetate (1.17M, 20 mL) at room temperature for 12 h. The solvent was removed under vacuum and the residue was trituated with ether. The product was diluted with methylene chloride and extracted with sodium hydroxide (0.5M). The organic phase was concentrated in vacuo and azeotroped with toluene to yield the product as a white solid. EI-MS m/z 334 (M+H)+

Workup

  1. customThe solvent was removed under vacuum
  2. additionThe product was diluted with methylene chloride
  3. extractionextracted with sodium hydroxide (0.5M)
  4. concentrationThe organic phase was concentrated in vacuo
  5. customazeotroped with toluene

Sources & evidence

ORD record
ord-c9480f5276074e2c8ae4682cb7157b8e
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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