Hydrochloric Acid → N-[2-(2-Propyl)-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl]-3-cyano-(S)-phenylalanine

HRID 1289483Notes

Reaction equation

HRID 1289483 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:34])[C@H:7]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[N:33])[CH:27]=1)[NH:8][S:9]([C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][N:18]([CH:22]([CH3:24])[CH3:23])[CH2:19]2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])C.Cl.CCOCC>O1CCOCC1>[CH3:24][CH:22]([N:18]1[CH2:17][CH2:16][C:15]2[C:20](=[CH:21][C:12]([S:9]([NH:8][C@H:7]([C:6]([OH:34])=[O:5])[CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[N:33])[CH:27]=3)(=[O:11])=[O:10])=[CH:13][CH:14]=2)[CH2:19]1)[CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 22885593N-[2-(2-Propyl)-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl]-3-cyano-(S)-phenylalanine ethyl ester

Product 1

HCID 67568068N-[2-(2-Propyl)-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl]-3-cyano-(S)-phenylalanineYield 83.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1M Aqueous sodium hydroxide solution (6.0 ml, 6 mmol) was added to a stirred solution of N-[2-(2-propyl)-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl]-3-cyano-(S)-phenylalanine ethyl ester (Preparation 25; 1.0 g, 2.19 mmol) in 1,4-dioxan (6.0 ml). After 2.5 hours at room temperature, the reaction mixture was neutralised using 1M hydrochloric acid (6.0 ml) and evaporated to dryness under reduced pressure. The residue was extracted successively with dichloromethane and a mixture of dichloromethane:2-propanol (9:1), then the combined extracts evaporated under reduced pressure to provide a material which, on trituration with ether, gave the title compound as a white powder (780 mg). Rf 0.06 (SS 3). m/e 428 (M+H)+.

Workup

  1. customevaporated to dryness under reduced pressure
  2. extractionThe residue was extracted successively with dichloromethane
  3. additiona mixture of dichloromethane:2-propanol (9:1)
  4. customthe combined extracts evaporated under reduced pressure
  5. customto provide a material which

Sources & evidence

ORD record
ord-a74a522180714381a1f3d2b82df06609
Source dataset
uspto-grants-1998_05
Patent number
US05750520

Reaction notes

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