HCID 53795060, compound → HCID 23436125, compound

HRID 2121177Notes

Reaction equation

HRID 2121177 reaction equation
C[O:2][C:3](=[O:35])[C:4]([C:12](=[O:34])[C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[O:21])=[CH:15][C:14]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([NH2:11])[CH2:5][CH2:6][S:7]([CH3:10])(=[O:9])=[O:8]>C1COCC1.O>[N:24]1[CH:25]=[CH:26][CH:27]=[C:22]([C:20]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([C:12]([C:4]([NH2:11])([CH2:5][CH2:6][S:7]([CH3:10])(=[O:8])=[O:9])[C:3]([OH:35])=[O:2])=[O:34])=[C:14]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:15]=2)=[O:21])[CH:23]=1

Participants

4

Reactant 1

HCID 53795060HCID 53795060, compound

Product 1

HCID 23436125HCID 23436125, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

The [4-(3-pyridylcarbonylamino)-2-phenylbenzoyl]-2-amino-4-(methylsulfonyl)butanoic acid methyl ester prepared in Example 203A (43 mg, 0.081 mmol) was dissolved in 3 mL of THF and a solution of LiOH monohydrate was in 1 mL of H2O was added. The reaction mixture was stirred at 25° C. for 1 hour and then was evaporated. Formic acid (1 mL) was added to acidify to pH=3. The reaction was then evaporated once again and 1 mL of H2O was added along with 5 mL of ethyl acetate to dissolve the mixture. The ethyl acetate layer was dried over Na2SO4, filtered and evaporated and the residue was lyophilized from acetonitrile/H2O to give [4-(3-pyridylcarbonylamino)-2-phenylbenzoyl]-2-amino-4-(methylsulfonyl)butanoic acid (36 mg, 88%) as a white solid. 1H NMR (300 mHz, CD3OD) δ 9.12 (d, 1H), 8.70 (d, 1H), 8.42 (dt, 1H), 7.85-7.80 (m, 2H), 7.65-7.40 (m, 8H), 4.50 (m, 1H), 2.90 (s, 3H), 2.88-2.80 (m, 1H), 2.70-2.58 (m, 1H), 2.35-2.20 (m, 1H), 2.10-1.95 (m, 1H). HRMS calcd C24H23N3SO6 MH+ 482.1386, found 482.1373.

Workup

  1. additionwas added
  2. customwas evaporated
  3. additionFormic acid (1 mL) was added
  4. customThe reaction was then evaporated once again
  5. addition1 mL of H2O was added along with 5 mL of ethyl acetate
  6. dissolutionto dissolve the mixture
  7. dry with materialThe ethyl acetate layer was dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-43753568029349e7a1c13fd0dd4c178c
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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