1,2-Dichloroethane → HCID 58951437, compound

HRID 1445752Notes

Reaction equation

HRID 1445752 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]([CH3:24])=[C:18]([CH2:20][C:21]([OH:23])=O)[N:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.[CH:29]1[CH:30]=C[C:32]2N(O)N=[N:35][C:33]=2[CH:34]=1.Cl.C[C@@H]1CCCN1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[O:16][C:17]([CH3:24])=[C:18]([CH2:20][C:21]([N:35]3[CH2:30][CH2:29][CH2:34][C@H:33]3[CH3:32])=[O:23])[N:19]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11147704(2R)-(-)-2-Methylpyrrolidine hydrochlorideHCID 222611715-Methyl-2-[4-(phenylmethoxy)phenyl]-4-oxazoleacetic acid

Product 1

HCID 58951437HCID 58951437, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of [2-(4-Benzyloxy-phenyl)-5-methyl-oxazol-4-yl]-acetic acid [CAS 403611-89-2] (2.2 g, 6.8 mmol) in CH2Cl2 (40 mL) is added EDC (1.57 g, 8.2 mmol) and HOBT (1.11 g, 8.2 mmol). After a few minutes, (R)-2-methylpyrrolidine hydrochloride [CAS 41720-98-3] (1.0 g, 8.2 mmol) and DIPEA (2.5 mL, 13.6 mmol) are added. The mixture is stirred at room temperature overnight. The mixture is partitioned between EtOAc and water. The aqueous phase is extracted with EtOAc (2×), and the combined organic phase is washed with brine, dried (Na2SO4), and concentrated. The residue is purified by flash chromatography [120 g SiO2, elute gradient 30% EtOAc/hexane to 80% EtOAc/hexane) to yield 1.25 g of the title compound as a yellow oil. MS (m/e): 391.2 (M+1)

Workup

  1. waitAfter a few minutes
  2. customThe mixture is partitioned between EtOAc and water
  3. extractionThe aqueous phase is extracted with EtOAc (2×)
  4. washthe combined organic phase is washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue is purified by flash chromatography [120 g SiO2
  8. washelute gradient 30% EtOAc/hexane to 80% EtOAc/hexane)

Sources & evidence

ORD record
ord-fc39cc0e88674219939956a339fcc1b6
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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