Methylthiourea → HCID 9911397, compound

HRID 1019065Notes

Reaction equation

HRID 1019065 reaction equation
[CH3:1][NH:2][C:3]([NH2:5])=[S:4].[CH3:6][O:7][C:8]([N:10]1[CH2:14][C@H:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:16]=2)[C@@:12]([C:30](=O)[CH2:31]Br)([CH3:29])[CH2:11]1)=[O:9]>CO>[CH3:6][O:7][C:8]([N:10]1[CH2:14][C@H:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)[CH:16]=2)[C@:12]([CH3:29])([C:30]2[N:5]=[C:3]([NH:2][CH3:1])[S:4][CH:31]=2)[CH2:11]1)=[O:9]

Participants

4

Reactant 2

HCID 2723704MethylthioureaHCID 12050979HCID 12050979, compound

Product 1

HCID 9911397HCID 9911397, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of 1-methyl-2-thiourea (0.038 g, 0.418 mmol) in methanol (1 mL), at 50° C., was added a solution of (3S,4R)-3-(2-bromoethanoyl)-4-(3-cyclopentyloxy-4-methoxyphenyl)-3-methyl-pyrrolidine-1-carboxylic acid methyl ester (0.19 g, 0.42 mmol) in methanol (1 mL). The temperature was raised to 70° C. and refluxed for 2 hours. The reaction mixture then was concentrated under reduced pressure and dissolved in acetonitrile-water (CH3CN—H2O) (1 mL) for purification by HPLC on a C18 column (Luna 10 μ, C18, 250×10 mm). Gradient elution of 50-100% acetonitrile-water (0.05% TFA) yielded the named product as a white powder after lyophilization (91 mg, 49%).

Workup

  1. temperaturerefluxed for 2 hours
  2. concentrationThe reaction mixture then was concentrated under reduced pressure
  3. dissolutiondissolved in acetonitrile-water (CH3CN—H2O) (1 mL) for purification by HPLC on a C18 column (Luna 10 μ, C18, 250×10 mm)
  4. washGradient elution of 50-100% acetonitrile-water (0.05% TFA)

Sources & evidence

ORD record
ord-00143dfa9c854cfe9aacfce579dddd45
Source dataset
uspto-grants-2002_11
Patent number
US06486186B2

Reaction notes

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