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4-Methylmorpholine → N-(2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl)-3-cyano-(S)-phenylalanine ethyl ester

HRID 343322
Notes
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Reaction equation

HRID 343322 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([S:15](Cl)(=[O:17])=[O:16])=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].Cl.[CH2:22]([O:24][C:25](=[O:37])[C@H:26]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]#[N:36])[CH:30]=1)[NH2:27])[CH3:23].[CH3:38]N1CCOCC1>ClCCl>[CH:25]([O:37][CH:13]([CH3:12])[CH3:14])([CH3:26])[CH3:38].[CH2:22]([O:24][C:25](=[O:37])[C@H:26]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]#[N:36])[CH:30]=1)[NH:27][S:15]([C:9]1[CH:8]=[C:7]2[C:12]([CH2:13][CH2:14][N:5]([C:3](=[O:4])[C:2]([F:20])([F:19])[F:1])[CH2:6]2)=[CH:11][CH:10]=1)(=[O:17])=[O:16])[CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 113249022-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chlorideHCID 700806773-cyano-(S)-phenylalanine ethyl ester hydrochloride

Product 2

HCID 7914Diisopropyl EtherHCID 54332895N-(2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl)-3-cyano-(S)-phenylalanine ethyl ester
Yield 194.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl chloride (Preparation 1; 7.72 g, 23.6 mmol) was added to a stirred, ice-cooled solution of 3-cyano-(S)-phenylalanine ethyl ester hydrochloride (Preparation 9; 6.0 g, 23.6 mmol) and N-methylmorpholine (5.0 g, 49.5 mmol) in dichloromethane (130 ml). After 18 hours at room temperature the reaction mixture was washed successively with water, 5% aqueous citric acid solution, water and saturated brine, dried (MgSO4) and evaporated under reduced pressure to give an oil which was dissolved in the minimum volume of dichloromethane. Treatment of this solution with diisopropyl ether provided the title compound (11.7 g) as a gum. Rf 0.56 (SS 8). m/e 510.

Workup

  1. washAfter 18 hours at room temperature the reaction mixture was washed successively with water, 5% aqueous citric acid solution, water and saturated brine
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. customto give an oil which

Sources & evidence

ORD record
ord-b2861e2c81ea4c75a0a31d84225611db
Source dataset
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05861393

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes