Hydrochloric Acid → HCID 135431012, compound

HRID 1289247Notes

Reaction equation

HRID 1289247 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([N:28]([CH3:52])[CH:29]2[C:33]3[CH:34]=[C:35]4[C:40](=[CH:41][C:32]=3[CH2:31][CH2:30]2)[N:39]=[C:38]([CH3:42])[N:37](COC(=O)C(C)(C)C)[C:36]4=[O:51])[CH:25]=[CH:24][C:3]=1[C:4]([NH:6][C@@H:7]([CH2:12][CH2:13][C:14]1[N:15]=[N:16][N:17]([CH2:19][C:20]([O:22]C)=[O:21])[N:18]=1)[C:8]([O:10]C)=[O:9])=[O:5].[OH-].[Na+].Cl>CO.O>[F:1][C:2]1[CH:27]=[C:26]([N:28]([CH3:52])[CH:29]2[C:33]3[CH:34]=[C:35]4[C:40](=[CH:41][C:32]=3[CH2:31][CH2:30]2)[N:39]=[C:38]([CH3:42])[NH:37][C:36]4=[O:51])[CH:25]=[CH:24][C:3]=1[C:4]([NH:6][C@@H:7]([CH2:12][CH2:13][C:14]1[N:15]=[N:16][N:17]([CH2:19][C:20]([OH:22])=[O:21])[N:18]=1)[C:8]([OH:10])=[O:9])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 86752525HCID 86752525, compound

Product 1

HCID 135431012HCID 135431012, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl (2S)-2-{o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]-benzamido}-4-(2-methoxycarbonylmethyltetrazol-5-yl)butyrate (87 mg) in methanol (2 ml) was slowly added an aqueous solution of NaOH (1N, 0.72 ml). The resultant solution was stirred at room temperature for 4 hours then more aqueous 1N NaOH (0.36 ml) was added and stirring was continued at room temperature for 1 hour. Next the solution was diluted with water (3 ml) and acidified to pH 4 with 1N hydrochloric acid. The precipitated solid was collected by filtration, washed with water (15 ml), and dried in vacuo over phosphorus pentoxide. There was thus obtained (2S)-2-{o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)-amino]benzamido}-4-(2-carboxymethyltetrazol-5-yl)butyric acid (57 mg) as a pale yellow solid, m.p. 196°-199° C.;

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with water (15 ml)
  3. dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-dfcbf25b66ea4146a532dca6b3f81817
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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