Hydrochloric Acid → 3,5-dichloro-O-[(2-phenyl)-benzoxazol-7-yl]methyl-L-tyrosine

HRID 1393370Notes

Reaction equation

HRID 1393370 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:40])[C@H:6]([CH2:14][C:15]1[CH:20]=[C:19]([Cl:21])[C:18]([O:22][CH2:23][C:24]2[C:32]3[O:31][C:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[N:29][C:28]=3[CH:27]=[CH:26][CH:25]=2)=[C:17]([Cl:39])[CH:16]=1)[NH:7]C(=O)C(F)(F)F.Cl>O1CCCC1.O>[Cl:21][C:19]1[CH:20]=[C:15]([CH:16]=[C:17]([Cl:39])[C:18]=1[O:22][CH2:23][C:24]1[C:32]2[O:31][C:30]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[N:29][C:28]=2[CH:27]=[CH:26][CH:25]=1)[CH2:14][C@@H:6]([C:5]([OH:40])=[O:4])[NH2:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 865983133,5-dichloro-N-trifluoroacetyl-O-[(2-phenyl)-benzoxazol-7-yl]methyl-L-tyrosine methyl ester

Product 1

HCID 98041283,5-dichloro-O-[(2-phenyl)-benzoxazol-7-yl]methyl-L-tyrosineYield 99.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.5 N Lithium hydroxide (4.5 ml, 2.25 mmol) was added to a solution of 3,5-dichloro-N-trifluoroacetyl-O-[(2-phenyl)-benzoxazol-7-yl]methyl-L-tyrosine methyl ester (246 mg, 0.434 mmol) in tetrahydrofuran (2 ml) at 5° C. and the mixture was reacted at 5° C. for 84 hrs. The reaction mixture was diluted with water, adjusted to pH 3-4 with 1N hydrochloric acid under ice cooling and allowed to stand at 5° C. The precipitates were collected by filtration, washed with water and then dried to give 3,5-dichloro-O-[(2-phenyl)-benzoxazol-7-yl]methyl-L-tyrosine (198 mg, 94%) as a colorless solid.

Workup

  1. customthe mixture was reacted at 5° C. for 84 hrs
  2. customto stand at 5° C
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-ad90756bd8e24a50ae326b50cc2583a7
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

Loading…