Triethylamine → HCID 178501032, compound

HRID 1670674Notes

Reaction equation

HRID 1670674 reaction equation
Cl.[NH2:2][C:3](N)([CH3:7])[C:4]([OH:6])=[O:5].[C:9]([C:14]1[CH:19]=[CH:18][C:17]([C@H:20]2[CH2:25][CH2:24][C@H:23]([C:26]([O:28][CH3:29])=[O:27])[CH2:22][CH2:21]2)=[CH:16][CH:15]=1)(=O)[C:10]([CH3:12])=O.C([N:32](CC)CC)C>CO>[CH3:29][O:28][C:26]([C@H:23]1[CH2:24][CH2:25][C@H:20]([C:17]2[CH:18]=[CH:19][C:14]([C:9]3[N:2]=[C:3]([C:4]([OH:6])=[O:5])[CH:7]=[N:32][C:10]=3[CH3:12])=[CH:15][CH:16]=2)[CH2:21][CH2:22]1)=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 86636662HCID 86636662, compoundHCID 178501037HCID 178501037, compound2×

Product 1

HCID 178501032HCID 178501032, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Diaminopropionic acid hydrochloride (496 mg, 3.52 mmol) was added to a stirred solution of methyl trans-4-(4-pyruvoylphenyl)cyclohexanecarboxylate (Intermediate 65-2, 844 mg, 2.93 mmol) and triethylamine (1.6 mL, 11.72 mmol) in MeOH (6 mL). After 48 h the reaction mixture was concentrated and the residue was triturated with ether to give the title compound (751 mg, 72%) as a solid that was used without further purification; 1H NMR δ9.04 (1H, s), 7.62 (2H, d), 7.40 (2H, d), 3.64 (3H, obs. s), 2.70-2.55 (1H, m), 2.66 (3H, s), 2.50-2.36 (1H, m), 2.08-1.96 (2H, m), 1.95-1.85 (2H, m), 1.65-1.45 (4H, m); MS 355.

Workup

  1. concentrationAfter 48 h the reaction mixture was concentrated
  2. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-62615e1577c24580bfb9ff7ffd2d918a
Source dataset
uspto-grants-2011_08
Patent number
US07994179B2

Reaction notes

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