Potassium Carbonate → HCID 86653645, compound

HRID 2064810Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([C:23]2[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=2)=[C:5]([C:7]([N:9]2[C@H:14]([CH2:15][NH:16]C(=O)C(F)(F)F)[CH2:13][C@H:12]3[C@@H:10]2[CH2:11]3)=[O:8])[N:6]=1.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+].CC(OC)(C)C>CO.CCOC(C)=O>[NH2:16][CH2:15][C@@H:14]1[CH2:13][C@H:12]2[C@H:10]([CH2:11]2)[N:9]1[C:7]([C:5]1[N:6]=[C:2]([NH2:1])[S:3][C:4]=1[C:23]1[CH:24]=[C:25]([CH3:29])[CH:26]=[CH:27][CH:28]=1)=[O:8]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of N-[(1S,3S,5S)-2-(2-amino-5-m-tolyl-thiazole-4-carbonyl)-2-aza-bicyclo[3.1.0]hex-3-ylmethyl]-2,2,2-trifluoro-acetamide (2.33 mmol) in MeOH (7.7 mL) is treated with a sat. aqueous K2CO3 solution (0.62 mL) and stirred at 60° C. for 5 h. After stirring for additional 16 h at RT the mixture is made basic by slow addition of aqueous NaOH solution (32%). Equal volumes of TBME and EtOAc are added and the mixture is stirred vigorously for 1 h. The layers are separated, the aqueous layer is extracted with a mixture of TBME and EtOAc and the combined organic layers are dried over Na2SO4. The solvents are removed in vacuo to give the desired product which is used without further purification. LC-MS (basic): tR=0.67 min; [M+H]+=329.0.

Workup

stirringAfter stirring for additional 16 h at RT the mixture
stirringthe mixture is stirred vigorously for 1 h
customThe layers are separated
extractionthe aqueous layer is extracted with a mixture of TBME and EtOAc
dry with materialthe combined organic layers are dried over Na2SO4
customThe solvents are removed in vacuo

Sources & evidence

ORD record: ord-eaf2007fce32461e8e073a5dde9fda87
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288435B2

Reaction notes

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