1-Isocyanato-2-phenylbenzene → HCID 57440631, compound

HRID 1882532Notes

Reaction equation

HRID 1882532 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13](=[O:22])[CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH:24]1[CH:29]=[CH:28][C:27]([C:30]2[C:35]([N:36]=[C:37]=[O:38])=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:26][CH:25]=1>CN1C(=O)CCC1>[C:1]([O:5][C:6](=[O:23])[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13](=[O:22])[CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([O:21][C:37](=[O:38])[NH:36][C:35]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:27]3[CH:26]=[CH:25][CH:24]=[CH:29][CH:28]=3)[CH2:19][CH2:20]2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2222801-Isocyanato-2-phenylbenzeneHCID 57440632HCID 57440632, compound

Product 1

HCID 57440631HCID 57440631, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
70 °C

Procedure

{(R)-1-[2-(4-Hydroxy-piperidin-1-yl)-acetyl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester (Intermediate Z1) (520 mg, 1.6 mmol) and 2-biphenylisocyanate (930 mg, 2.65 mmol) are dissolved in NMP (2 ml) and heated to 70° C. overnight. Purification is carried out by reverse phase column chromatography (Isolute™ C18, 0-100% MeOH in water −0.1% TFA). The fractions containing the product are concentrated in vacuo to remove the acetonitrile and the aqueous is treated with saturated sodium bicarbonate solution. The product is extracted with DCM and the combined organic portions are concentrated in vacuo to afford the title product. [MH+ 523.24].

Workup

  1. customPurification
  2. additionThe fractions containing the product
  3. concentrationare concentrated in vacuo
  4. customto remove the acetonitrile
  5. additionthe aqueous is treated with saturated sodium bicarbonate solution
  6. extractionThe product is extracted with DCM
  7. concentrationthe combined organic portions are concentrated in vacuo

Sources & evidence

ORD record
ord-c4c77ccc8f2449bbac8ec497c58b6b8b
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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