Hydrochloric Acid → (S)-1-(5-Formylthiazol-2-yl)pyrrolidine-2-carboxylic acid

HRID 1755472Notes

Reaction equation

HRID 1755472 reaction equation
[CH:1]([C:3]1[S:7][C:6]([N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[C:13]([O:15]C(C)(C)C)=[O:14])=[N:5][CH:4]=1)=[O:2].Cl.CCOCC>C(Cl)Cl>[CH:1]([C:3]1[S:7][C:6]([N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[C:13]([OH:15])=[O:14])=[N:5][CH:4]=1)=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 131733675(S)-ter-Butyl 1-(5-formylthiazol-2-yl)pyrrolidine-2-carboxylate

Product 1

HCID 89858146(S)-1-(5-Formylthiazol-2-yl)pyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure as described in Example 68, except using material from Example 79 (33.4 mg, 0.118 mmol), anhydrous CH2Cl2 (3 mL), HCl, 1.0M in Et2O (6 mL, 6.0 mmol) stirring at room temp for 48 h, the title compound (quantitative yield) is isolated as an HCl salt that is used directly “as is” in the next step. LC/MS (Condition A): ret. T=1.88 min, (M+H)+ 227.05.

Sources & evidence

ORD record
ord-e83a2aeea0bc44638ad264c6d5341e35
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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