HCID 69288006, compound → HCID 23085247, compound

HRID 2375806Notes

Reaction equation

HRID 2375806 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:23][C:24]2[CH:28]=[C:27]([C:29]3[S:30][C:31]([Cl:34])=[CH:32][CH:33]=3)[O:26][N:25]=2)[C:8]([CH3:22])=[C:9]([S:12]([N:15]2[CH2:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)(=[O:14])=[O:13])[C:10]=1[CH3:11])=[O:5])C>C1COCC1.O>[Cl:34][C:31]1[S:30][C:29]([C:27]2[O:26][N:25]=[C:24]([CH2:23][N:7]3[C:8]([CH3:22])=[C:9]([S:12]([N:15]4[CH2:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)(=[O:14])=[O:13])[C:10]([CH3:11])=[C:6]3[C:4]([OH:5])=[O:3])[CH:28]=2)=[CH:33][CH:32]=1

Participants

3

Reactant 1

HCID 69288006HCID 69288006, compound

Product 1

HCID 23085247HCID 23085247, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of [5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-3,5-dimethyl-4-([1,4]oxazepane-4-sulfonyl)-1H-pyrrole-2-carboxylic acid ethyl ester (100 mg) in 20 mL of THF/water(3:1) was added LiOH monohydrate (200 mg) The mixture was stirred for 2h at 45° C. and for 6 h at 60° C. whereupon it was cooled to RT, concentrated, acidified with 2M HCl to pH=2 and extracted with DCM (3×30 mL). The combined organic layers were dried (MgSO4) and concentrated to give crude 1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-3,5-dimethyl-4-([1,4]oxazepane-4-sulfonyl)-1H-pyrrole-2-carboxylic acid (80 mg) which was used directly in the next step.

Workup

  1. concentrationconcentrated
  2. extractionextracted with DCM (3×30 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1e86095b05904d6e83abb47eb9688800
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

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