Sodium Hydroxide → HCID 136351293, compound

HRID 1289242Notes

Reaction equation

HRID 1289242 reaction equation
[F:1][C:2]1[CH:24]=[C:23]([N:25]([CH3:49])[CH:26]2[C:30]3[C:31](C)=[C:32]4[C:37](=[CH:38][C:29]=3[CH2:28][CH2:27]2)[N:36]=[C:35]([CH3:39])[N:34](OC(=O)C(C)(C)C)[C:33]4=[O:47])[CH:22]=[CH:21][C:3]=1[C:4]([NH:6][C@@H:7]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][CH:12]=1)[C:8]([OH:10])=[O:9])=[O:5].[OH-].[Na+]>CO>[F:1][C:2]1[CH:24]=[C:23]([N:25]([CH3:49])[CH:26]2[C:30]3[CH:31]=[C:32]4[C:37](=[CH:38][C:29]=3[CH2:28][CH2:27]2)[N:36]=[C:35]([CH3:39])[NH:34][C:33]4=[O:47])[CH:22]=[CH:21][C:3]=1[C:4]([NH:6][C@@H:7]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][CH:12]=1)[C:8]([OH:10])=[O:9])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86752523HCID 86752523, compound

Product 1

HCID 136351293HCID 136351293, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2S)-2-{o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-3-pivaloyloxy-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzamido}-2-[p-(carboxymethyl)phenyl]acetic acid (0.14 g, 0.2 mmol) in 1 ml of methanol containing 0.6 ml of 1N NaOH was stirred for 90 minutes at room temperature. After dilution with water and filtration the pH was adjusted to 2.5 with 2N HCl . The resulting solid was filtered off, washed with water, dried and triturated with ether to give (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}-2-[p-(carboxymethyl)phenyl]acetic acid (0.103 g, 93%) as a white solid, m.p. 196°-200° C.;

Workup

  1. filtrationAfter dilution with water and filtration the pH
  2. filtrationThe resulting solid was filtered off
  3. washwashed with water
  4. customdried
  5. customtriturated with ether

Sources & evidence

ORD record
ord-ada06f2917144b7abe3d607323819bee
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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