Diethyl Ether → HCID 42641447, compound

HRID 600331Notes

Reaction equation

HRID 600331 reaction equation
[C:1]([C@@H:3]([NH:25][C:26]([C@@H:28]1[CH2:33][CH2:32][CH2:31][CH2:30][N:29]1C(OC(C)(C)C)=O)=[O:27])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17](=[O:19])[N:16]([CH2:20][CH2:21][O:22][CH3:23])[C:15]=3[CH:24]=2)=[CH:7][CH:6]=1)#[N:2].C(OCC)C>C(O)=O>[C:1]([C@@H:3]([NH:25][C:26]([C@@H:28]1[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]1)=[O:27])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17](=[O:19])[N:16]([CH2:20][CH2:21][O:22][CH3:23])[C:15]=3[CH:24]=2)=[CH:7][CH:6]=1)#[N:2]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 57999643HCID 57999643, compound

Product 1

HCID 42641447HCID 42641447, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of (S)-tert-butyl 2-((S)-1-cyano-2-(4-(3-(2-methoxyethyl)-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethylcarbamoyl)piperidine-1-carboxylate (38 mg) in formic acid (1 mL) was stirred at 50° C. for 10 min. The solvent was removed in vacuo and the residue was purified by flash silica chromatography eluting with 1:24 2M ammonia in methanol/DCM to give, after trituration with diethyl ether, the title compound (27 mg) as a pale yellow solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash silica chromatography
  3. washeluting with 1:24 2M ammonia in methanol/DCM
  4. customto give

Sources & evidence

ORD record
ord-9843c4b81a384289a28ba2a12d60edd2
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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