Hydrochloric Acid → 3-amino-N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]-6-methylbenzoyl]-L-alanine, methyl ester hydrochloride

HRID 393058Notes

Reaction equation

HRID 393058 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:31]=[C:30]([C:32]([NH:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([OH:42])[CH:37]=2)=[O:33])[CH:29]=[C:28]([CH3:43])[C:10]=1[C:11]([NH:13][C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:15][NH:16]C(OC(C)(C)C)=O)=[O:12].Cl.C(#N)C>ClCCl>[ClH:8].[NH2:16][CH2:15][C@@H:14]([C:24]([O:26][CH3:27])=[O:25])[NH:13][C:11](=[O:12])[C:10]1[C:28]([CH3:43])=[CH:29][C:30]([C:32]([NH:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([OH:42])[CH:37]=2)=[O:33])=[CH:31][C:9]=1[Cl:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 131723027N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]-6-methylbenzoyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]-L-alanine, methyl ester

Product 1

HCID 1317230283-amino-N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]-6-methylbenzoyl]-L-alanine, methyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (20 mL) was added to a solution of N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]-6-methylbenzoyl]-3-[[(1,1-dimethylethoxy)carbonyl]amino]-L-alanine, methyl ester (800 mg, 1.54 mmol) in dichloromethane (20 mL). The solution was stirred at room temperature for 1 h. The reaction mixture was concentrated, azeotroped three times with dichloromethane/hexanes, and then held under high vacuum for 35 min. 1 M HCl (4.6 mL, 4.6 mmol) was added, along with acetonitrile (4 mL) and the mixture was freeze-dried overnight to give crude 3-amino-N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]-6-methylbenzoyl]-L-alanine, methyl ester hydrochloride (0.85 g, 120% of the theoretical amount).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customazeotroped three times with dichloromethane/hexanes
  3. waitheld under high vacuum for 35 min
  4. customthe mixture was freeze-dried overnight

Sources & evidence

ORD record
ord-31c81c63ee154812972fb4d67659b540
Source dataset
uspto-grants-2004_10
Patent number
US06803384B2

Reaction notes

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