Lithium Hydroxide → HCID 21710722, compound

HRID 1872179Notes

Reaction equation

HRID 1872179 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:28])[C:6]([NH:15][C:16]([C:18]1[NH:19][C:20]2[C:25]([CH:26]=1)=[CH:24][C:23]([Cl:27])=[CH:22][CH:21]=2)=[O:17])([CH3:14])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCCC1>[Cl:27][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18]([C:16]([NH:15][C:6]([CH3:14])([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:5]([OH:28])=[O:4])=[O:17])=[CH:26]2

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 54395516HCID 54395516, compound

Product 1

HCID 21710722HCID 21710722, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous 2N LiOH (0.10 ml, 0.50 mmol) was added to a solution of (2RS)-[(5-chloro-1H-indole-2-carbonyl)-amino]-2-methyl-3-phenyl-propionic acid methyl ester (132 mg, 0.36 mmol) in tetrahydrofuran (8 ml) at 25° C. The resulting solution was stirred for 1 hour, concentrated and the residue dissolved in ethyl acetate and water (15 ml). The pH was adjusted to 1 with 2 N HCl at 0° C. The organic layer was separated, washed with water, brine and dried giving a foam which was used without further purification (129 mg, 102%): HPLC (60/40) 4.42 minutes (99%); TSPMS 357/359 (MH+, 100%);

Workup

  1. concentrationconcentrated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. customwas adjusted to 1 with 2 N HCl at 0° C
  4. customThe organic layer was separated
  5. washwashed with water, brine
  6. customdried
  7. customgiving a foam which
  8. customwas used without further purification (129 mg, 102%)
  9. custom(60/40) 4.42 minutes (99%)

Sources & evidence

ORD record
ord-8c0452f45991454f995fb0ba9cc13d98
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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