Ammonium Chloride → HCID 67692298, compound

HRID 343333Notes

Reaction equation

HRID 343333 reaction equation
[Na].[CH2:2]([O:4][C:5]([C@H:7]1[CH2:12][C:11]([CH3:13])=[CH:10][CH2:9][N:8]1[C:14](=[O:40])[C@H:15]([CH2:31][C:32]1[CH:37]=[CH:36][N:35]=[C:34]([C:38]#[N:39])[CH:33]=1)[NH:16][S:17]([C:20]1[CH:29]=[C:28]2[C:23]([CH2:24][CH2:25][N:26]([CH3:30])[CH2:27]2)=[CH:22][CH:21]=1)(=[O:19])=[O:18])=[O:6])[CH3:3].[Cl-:41].[NH4+:42]>C(O)C>[ClH:41].[CH2:2]([O:4][C:5]([C@H:7]1[CH2:12][C:11]([CH3:13])=[CH:10][CH2:9][N:8]1[C:14](=[O:40])[C@H:15]([CH2:31][C:32]1[CH:37]=[CH:36][N:35]=[C:34]([C:38](=[NH:42])[NH2:39])[CH:33]=1)[NH:16][S:17]([C:20]1[CH:29]=[C:28]2[C:23]([CH2:24][CH2:25][N:26]([CH3:30])[CH2:27]2)=[CH:22][CH:21]=1)(=[O:19])=[O:18])=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 67692231HCID 67692231, compound

Product 1

HCID 67692298HCID 67692298, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium metal (30 mg, 1.3 mmol) was added to a stirred solution of 4-methyl-1-[N-(2-methyl-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl)-3-(2-cyano-4-pyridyl)-(S)-alanyl]-1,2,3,6-tetrahydropyridine-2(R)-carboxylic acid ethyl ester (Preparation 54; 243 mg, 0.44 mmol) in ethanol (4 ml) at room temperature. After 1 hour, ammonium chloride (140 mg, 2.6 mmol) was added and the resulting mixture stirred for 18 hours and then filtered. Evaporation under reduced pressure of the filtrate followed by purification of the residue by chromatography on silica gel, using dichloromethane:methanol:0.880 aqueous ammonia solution (90:10:1) as eluent, furnished the title compound (176 mg) as a foam. Rf 0.21 (SS 13). Found: C,55.64; H,6.31; N,13.47. C28H36N6O5S; HCl requires C,55.56; H,6.16; N,13.88%.

Workup

  1. filtrationfiltered
  2. customEvaporation under reduced pressure of the filtrate
  3. customfollowed by purification of the residue by chromatography on silica gel

Sources & evidence

ORD record
ord-92ce8776f87240148da7534a19891f32
Source dataset
uspto-grants-1999_01
Patent number
US05861393

Reaction notes

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