Hydrochloric Acid → (S)-2-Amino-N-(3-(5-formylthiazol-2-ylamino)propyl)propanamide

HRID 1755466Notes

Reaction equation

HRID 1755466 reaction equation
[CH:1]([C:3]1[S:7][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:24])[C@@H:14]([NH:16]C(=O)OC(C)(C)C)[CH3:15])=[N:5][CH:4]=1)=[O:2].Cl.C(OCC)C>C(Cl)Cl>[NH2:16][C@@H:14]([CH3:15])[C:13]([NH:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]1[S:7][C:3]([CH:1]=[O:2])=[CH:4][N:5]=1)=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 86700112(S)-tert-Butyl 1-(3-(5-formylthiazol-2-ylamino)propylamino)-1-oxopropan-2-ylcarbamate

Product 1

HCID 86700111(S)-2-Amino-N-(3-(5-formylthiazol-2-ylamino)propyl)propanamideYield 137.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure as described in Example 68, except using material from Example 69 (265 mg, 0.743 mmol), CH2Cl2 (50 mL), HCl, 11.0M in diethyl ether (5 mL, 5.00 mmol) and stirring at room temp for 2.5 days, 262 mg (quantitative yield) of the title compound is obtained as a pale yellow solid, as a bis HCl salt by weight. LC/MS (Condition A): ret. T=0.93 min, (M+H)+ 257.14.

Sources & evidence

ORD record
ord-691d65edd76342adb9ba7fca985f8d8c
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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