Triethylamine → HCID 69034550, compound

HRID 1242818Notes

Reaction equation

HRID 1242818 reaction equation
Cl.[NH:2]1[CH2:11][C@H:9]([OH:10])[CH2:8][C@H:3]1[CH2:4][C:5]([OH:7])=[O:6].C(N(CC)CC)C.[C:19]1([C:25]2[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O.O1CCCC1.CC(C)=O.C(OCC)(=O)C>[C:25]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:26]=[CH:27][C:28]([C:29]([N:2]2[CH2:11][C@H:9]([OH:10])[CH2:8][C@H:3]2[CH2:4][C:5]([OH:7])=[O:6])=[O:30])=[CH:32][CH:33]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 841514-Phenylbenzoyl chlorideHCID 16211054L-beta-Homohydroxyproline hydrochloride

Product 1

HCID 69034550HCID 69034550, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 21584569Ethylacetate acetoneSolvent

Procedure

To a solution of commercial L-beta-homohydroxyproline hydrochloride (245 mg, 1.35 mmol), triethylamine (1.13 ml, 8.09 mmol) in water (0.8 ml) and tetrahydrofuran (2 ml) at 0° C. under argon, was added dropwise a solution of 4-phenylbenzoyl chloride (438 mg, 2.02 mmol) in tetrahydrofuran (1 ml). The reaction mixture was allowed to warm to room temperature and was stirred 18 hours. It was then diluted with acetone-ethyl acetate (1-2) and washed with HCl 1N. The organic phase was dried (MgSO4) and concentrated to afford a mixture of desired product and 4-phenylbenzoyl acid. A small quantity of acid could be obtained by precipitation with ethyl acetate.

Workup

  1. washwashed with HCl 1N
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated
  4. customto afford

Sources & evidence

ORD record
ord-6d48a76b20da4c46bb58eddcd402dbd0
Source dataset
uspto-grants-2006_10
Patent number
US07115754B2

Reaction notes

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