Lithium hydroxide, monohydrate → HCID 59378087, compound

HRID 1639569Notes

Reaction equation

HRID 1639569 reaction equation
O.[OH-].[Li+].C([O:6][C:7](=[O:32])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:23](=[O:31])[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:14](=[O:22])[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)C>O.C(O)C>[C:16]1([NH:15][C:14]([CH:13]([C:23](=[O:31])[NH:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]([OH:32])=[O:6])=[O:22])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59378084HCID 59378084, compound

Product 1

HCID 59378087HCID 59378087, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of lithium hydroxide monohydrate (0.17 g, 4.05 mmol) in water (5 mL) was added to a stirred solution of 7,7-bis-phenylcarbamoyl-heptanoic acid ethyl ester (16a) (1.07 g, 2.7 mmol) in ethanol (50 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 16 hours. The solvent was removed under reduced pressure and the resulting residue was taken up in water (50 mL), washed with ethyl acetate (60 mL) and acidified with 1 M hydrochloric acid. The aqueous layer was extracted with ethyl acetate (3×60 mL), and the combined extracts were dried (MgSO4), filtered and organic solvent evaporated to give 7,7-bis-phenylcarbamoyl-heptanoic acid (16b) as a white solid (0.95 g, 95%); Rf=0.25 (3:1, petroleum ether 60-80° C.:ethyl acetate); 1H NMR (300 MHz, CDCl3): δ 9.83 (2H, s, NH), 7.56 (4H, d, J=7.8 Hz, Ar—H), 7.32 (4H, t, J=8.1 Hz, Ar—H), 7.14 (2H, t, J=7.6 Hz, Ar—H), 3.43 (1H, t, J=7.2 Hz, COCH), 2.58 (2H, t, J=7.1 Hz, CH2CO), 1.86 (2H, br m, CHCH2CH2CH2CH2), 1.49 (2H, t, J=7.1 Hz, CHCH2), 1.33 (4H, br m, CHCH2CH2CH2); 13C NMR (75 MHz, CDCl3): δ 172.10 (CO), 170.17 (CO), 137.13 (quaternary Ar—C), 128.73 (Ar—C—H), 124.68 (Ar—C—H), 120.52 (Ar—C—H), 56.32 (COCH), 34.18 (CH2CO), 33.43 (CHCH2CH2CH2), 28.32 (CHCH2), 27.23 (CHCH2CH2), 24.54 (CHCH2CH2CH2CH2).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed with ethyl acetate (60 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×60 mL)
  4. dry with materialthe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customorganic solvent evaporated

Sources & evidence

ORD record
ord-b4d47c5da76344c0a752c920a0495371
Source dataset
uspto-grants-2012_02
Patent number
US08110577B2

Reaction notes

Loading…