Lithium Hydroxide → HCID 44816532, compound

HRID 1696887Notes

Reaction equation

HRID 1696887 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][C@@H:14]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[Cl:35])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:13]=2[CH:12]=[CH:11][CH:10]=1)(C)(C)C.[OH-].[Li+]>O1CCCC1>[Cl:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:26]1[CH:27]=[CH:28][C:23]([S:20]([NH:19][C@@H:14]2[CH2:15][CH2:16][CH2:17][C:18]3[C:9]([O:8][CH2:7][C:6]([OH:36])=[O:5])=[CH:10][CH:11]=[CH:12][C:13]2=3)(=[O:21])=[O:22])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59192545HCID 59192545, compound

Product 1

HCID 44816532HCID 44816532, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-[5-(2′-Chloro-biphenyl-4-sulfonylamino)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid tert-butyl ester was treated with aqueous lithium hydroxide (0.2 M, 1 mL) in tetrahydrofuran (1 mL) overnight, at room temperature. The reaction mixture was concentrated in vacuo. Reverse phase HPLC (Pursuit C-18, 20×150 mm, water/acetonitrile/0.05% trifluoroacetic acid) gave (R)-[5-(2′-chloro-biphenyl-4-sulfonylamino)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid (8.5 mg, 43% over two steps). MS cald. for C24H22ClNO5S 471, obsd. 472 [(M+H)+].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-c15c4a1bc2d440b7abb8e2b268687f40
Source dataset
uspto-grants-2012_04
Patent number
US08163781B2

Reaction notes

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