Lithium hydroxide, monohydrate → [(4-Chloro-benzyl)-(1-{3-[7-(1-hydroxy-1-methyl-ethyl)-11H-10-oxa-1-aza-dibenzo[a,d]cyclohepten-5-ylidene]-propyl}-pyrolidin-3-yl)-amino]-acetic acid

HRID 242634Notes

Reaction equation

HRID 242634 reaction equation
C[O:2][C:3](=[O:41])[CH2:4][N:5]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)[CH:6]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH:13]=[C:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[N:24][C:19]=3[CH2:18][O:17][C:16]3[CH:25]=[CH:26][C:27]([C:29]([OH:32])([CH3:31])[CH3:30])=[CH:28][C:15]2=3)[CH2:7]1.O.[OH-].[Li+]>C1COCC1.O>[Cl:40][C:37]1[CH:36]=[CH:35][C:34]([CH2:33][N:5]([CH2:4][C:3]([OH:41])=[O:2])[CH:6]2[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH:13]=[C:14]3[C:20]4[CH:21]=[CH:22][CH:23]=[N:24][C:19]=4[CH2:18][O:17][C:16]4[CH:25]=[CH:26][C:27]([C:29]([OH:32])([CH3:31])[CH3:30])=[CH:28][C:15]3=4)[CH2:7]2)=[CH:39][CH:38]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66758164[(4-Chloro-benzyl)-(1-{3-[7-(1-hydroxy-1-methyl-ethyl)-11H-10-oxa-1-aza-dibenzo[a,d]cyclohepten-5-ylidene]-propyl}-pyrrolidin-3-yl)-amino]-acetic Acid Methyl Ester

Product 1

HCID 66757921[(4-Chloro-benzyl)-(1-{3-[7-(1-hydroxy-1-methyl-ethyl)-11H-10-oxa-1-aza-dibenzo[a,d]cyclohepten-5-ylidene]-propyl}-pyrolidin-3-yl)-amino]-acetic acid

Reagents, catalysts & solvents 1

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

Procedure

To a solution of [(4-Chloro-benzyl)-(1-{3-[7-(1-hydroxy-1-methyl-ethyl)-11H-10-oxa-1-aza-dibenzo[a,d]cyclohepten-5-ylidene]-propyl}-pyrrolidin-3-yl)-amino]-acetic acid methyl ester (116 mg, 0.2 mmol) in THF:H2O (4:1, 10 mL total volume) was added lithium hydroxide monohydrate (17 mg, 0.4 mmol). The resultant solution was stirred at rt for 3 h. The reaction solution was quenched with 1N HCl and extracted with ethyl ether, dried over MgSO4, filtered and concentrated. The final product was filtered through filter paper and re-concentrated. This product was submitted without further purification. LCMS (retention time=1.72, ES+562); 1H NMR (CD3OD): δ 8.48 (1H, d), 7.78 (1H, d), 7.48 (2H, m), 7.31 (5H, m), 6.76 (1H, d), 6.15 (1H, t), 3.85 (2H, dd), 3.60 (2H, m), 3.30 (7H, m), 3.24 (1H, s), 3.18 (1H, m), 3.06 (1H, m), 2.58 (1H, m), 2.48 (1H, t), 2.06 (2H, m), 1.50 (6H, s).

Workup

  1. customThe reaction solution was quenched with 1N HCl
  2. extractionextracted with ethyl ether
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. filtrationThe final product was filtered
  7. filtrationthrough filter paper
  8. concentrationre-concentrated
  9. customThis product was submitted without further purification

Sources & evidence

ORD record
ord-a89c12be58b940158a515c014c5cb50b
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

Loading…