Hydrochloric Acid → (E)-2-{4-[2-(-tert-Butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-5-chloro-pentanoic acid

HRID 220176Notes

Reaction equation

HRID 220176 reaction equation
C[O:2][C:3](=[O:34])[CH:4]([C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17](=[O:33])[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2NC(OC(C)(C)C)=O)=[CH:11][CH:10]=1)[CH2:5][CH2:6][CH2:7][Cl:8].[Li+].[OH-:36].Cl>CO.O>[C:4]([O:36][C:17]([NH:18][N:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:17](/[CH:16]=[CH:15]/[C:12]1[CH:13]=[CH:14][C:9]([CH:4]([CH2:5][CH2:6][CH2:7][Cl:8])[C:3]([OH:2])=[O:34])=[CH:10][CH:11]=1)=[O:33])=[O:33])([CH3:9])([CH3:5])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59238291(E)-2-{4-[2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-5-chloro-pentanoic acid methyl ester

Product 1

HCID 67231601(E)-2-{4-[2-(-tert-Butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-5-chloro-pentanoic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of (E)-2-{4-[2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-5-chloro-pentanoic acid methyl ester (48.7 mg, 10 mmol) in MeOH/H2O (4:1) (2 mL), LiOH (24 mg, 100 mmol) was added. After the solution was stirred at room temperature for 5 h, the solution was neutralized with 2N HCl to pH 5-6. The mixture was evaporated to dryness under reduced pressure, then EtOAc (10 mL) was added. The organic layer was washed with brine, dried with Na2SO4, filtered, and evaporated to obtain of a yellow solid product without further purification. MS: calc'd 473 (MH+), exp 473 (MH+). 1H NMR (400 MHz, DMSO-d6) 12.50 (s, 1H), 9.73 (s, 1H), 8.50 (s, 1H), 6.89-7.64 (m, 10H), 3.61 (m, 3H), 1.55-2.10 (m, 4H), 1.46 (s, 9H).

Workup

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. additionEtOAc (10 mL) was added
  3. washThe organic layer was washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto obtain of a yellow solid product without further purification

Sources & evidence

ORD record
ord-06f672c9f4084e9a9fa90d1f6068ff3b
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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