Hydrochloric Acid → (5-[(1S)-1-benzyloxycarbonylamino-ethyl]-3-benzyl-2-oxo-cyclohept-4-en-1-yl)-ethanoic acid

HRID 1755817Notes

Reaction equation

HRID 1755817 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]([O:24]C)=[O:23])[C:17](=[O:26])[CH:16]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:15]=1)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCOCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]1[CH2:20][CH2:19][CH:18]([CH2:21][C:22]([OH:24])=[O:23])[C:17](=[O:26])[CH:16]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:15]=1)[CH3:13])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86748875methyl (5-[(1S)-1-benzyloxycarbonylamino-ethyl]-3-benzyl-2-oxo-cyclohept-4-en-1-yl)-ethanoate

Product 1

HCID 54027587(5-[(1S)-1-benzyloxycarbonylamino-ethyl]-3-benzyl-2-oxo-cyclohept-4-en-1-yl)-ethanoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of the above ester (35) (1.2 g) in dioxane (12 mL) was added a solution of NaOH (5.3 mL, 1N in H2O). After stirring for 4 h at room temperature 1N HCl (5.3 mL) was added and the reaction extracted with ethyl acetate, washed with saturated NaCl, dried over MgSO4 and evaporated. The product (37) was obtained by flash chromatography (silica gel, 98:2:0.1 CHCl3 :MeOH:HOAc) (1.0 g, 86%). TLC Rf 0.53 (95:4:1 CHCl3 :MeOH:HOAc); MS DC I/NH3 (M+H)+ =436.3; 1H NMR (CDCl3) δ1.13(3H, d, J=7 Hz ), 1.6-3.3 (9H, m), 3.65 (1H, m), 4.1 (1H, br m), 5.1 (2H, s), 5.45(1H, d), 7.2(5H, s), 7.35(5H, s), 10.65 (1H, br s).

Workup

  1. additionwas added
  2. extractionthe reaction extracted with ethyl acetate
  3. washwashed with saturated NaCl
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-a1a359c522584514871aa836d8ce3a96
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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