Methylparaben → Tert-butyl 4-(4-(4-methoxycarbonylphenoxymethyl)thiazol-2-yl]piperazine-1-carboxylate

HRID 1016473Notes

Reaction equation

Cl[CH2:2][C:3]1[N:4]=[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[S:6][CH:7]=1.[OH:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:29][O:28][C:26]([C:25]1[CH:30]=[CH:31][C:22]([O:21][CH2:2][C:3]2[N:4]=[C:5]([N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)[S:6][CH:7]=2)=[CH:23][CH:24]=1)=[O:27]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of tert-butyl 4-(4-chloromethylthiazol-2-yl)piperazine-1-carboxylate (820 mg, 2.58 mmol) and methyl 4-hydroxybenzoate (395 mg, 2.58 mmol) in DMF was treated with potassium carbonate (360 mg, 2.6 mmol). The mixture was stirred at 70° C. for approximately 12 hours and then concentrated under vacuum. The residue was partitioned between ethyl acetate and water and the or organic phase was separated, washed with brine, dried over sodium sulfate and concentrated. The residue was crystallized from a mixture of ethyl acetate/hexanes to provide tert-butyl 4-[4-(4-methoxycarbonyl-phenoxymethyl)thiazol-2-yl]piperazine-1-carboxylate (830 mg, 74% yield). HNMR (dmso-d6): HNMR (dmso-d6): 7.91 (2H, d), 7.13 (2H, d), 6.91 (1H, s), 5.00 (2H, s), 3.81 (3H, s), 3.41 (8H, m), 1.41 (9H, s).

Workup

concentrationconcentrated under vacuum
customThe residue was partitioned between ethyl acetate and water
customthe or organic phase was separated
washwashed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was crystallized from a mixture of ethyl acetate/hexanes

Sources & evidence

ORD record: ord-c8a35b74f0aa4f918b5afedc8d55591f
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06476026B1

Reaction notes

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