Lithium hydroxide, monohydrate → HCID 71119261, compound

HRID 633813Notes

Reaction equation

HRID 633813 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([CH:8]1[CH2:12][CH:11]([NH:13][C:14]([C:16]2[CH:17]=[CH:18][C:19]3[S:24][CH2:23][C:22](=[O:25])[NH:21][C:20]=3[CH:26]=2)=[O:15])[CH2:10][N:9]1[CH2:27][CH:28]1[CH2:41][C:40]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([O:42][CH3:43])[CH:38]=3)[N:33]=[CH:32][C:31]=2[O:30][CH2:29]1)=[O:7]>O1CCCC1.O>[CH3:43][O:42][C:37]1[CH:38]=[C:39]2[C:34](=[CH:35][CH:36]=1)[N:33]=[CH:32][C:31]1[O:30][CH2:29][CH:28]([CH2:27][N:9]3[CH2:10][CH:11]([NH:13][C:14]([C:16]4[CH:17]=[CH:18][C:19]5[S:24][CH2:23][C:22](=[O:25])[NH:21][C:20]=5[CH:26]=4)=[O:15])[CH2:12][CH:8]3[C:6]([OH:7])=[O:5])[CH2:41][C:40]2=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71118984HCID 71118984, compound

Product 1

HCID 71119261HCID 71119261, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (5.5 mg, 0.13 mmol, 1.5 eq) is added at room temperature to a stirred solution of 1-(6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-3-ylmethyl)-4-[(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carbonyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester (70 mg, 0.09 mmol, 1.0 eq) in tetrahydrofuran (2 mL) and water (1 mL). After 1 hour stirring at room temperature, the reaction mixture is concentrated and purified by preparative HPLC to afford 1-(6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-3-ylmethyl)-4-[(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carbonyl)-amino]-pyrrolidine-2-carboxylic acid as a white lyophilized powder (14 mg, 28% yield).

Workup

  1. concentrationthe reaction mixture is concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-4425949a1f49410e9e00e4b2e9a0d719
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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