1,2-Dichloroethane → (S)-tert-Butyl 2-((S)-2-(2-(5-formylthiazol-2-ylamino)acetamido)propanamido)propanoate

HRID 1755483Notes

Reaction equation

HRID 1755483 reaction equation
[CH:1]([C:3]1[S:7][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[N:5][CH:4]=1)=[O:2].Cl.Cl.[NH2:15][C@@H:16]([CH3:29])[C:17]([NH:19][C@@H:20]([CH3:28])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:18].ON1C2N=CC=CC=2N=N1.C(Cl)CCl>C(Cl)Cl>[CH:1]([C:3]1[S:7][C:6]([NH:8][CH2:9][C:10]([NH:15][C@@H:16]([CH3:29])[C:17]([NH:19][C@@H:20]([CH3:28])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:18])=[O:12])=[N:5][CH:4]=1)=[O:2]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 181649HOAtHCID 15600049tert-butyl (2S)-2-[(2S)-2-aminopropanamido]propanoate hydrochlorideHCID 867000852-((5-Formylthiazol-2-yl)amino)acetic acid

Product 1

HCID 86700126(S)-tert-Butyl 2-((S)-2-(2-(5-formylthiazol-2-ylamino)acetamido)propanamido)propanoateYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the general procedure as described in Example 24, except using 2-(5-formylthiazol-2-ylamino)acetic acid, 1.00 HCl (582 mg, 2.62 mmol), (S)-tert-butyl 2-((S)-2-aminopropanamido)propanoate hydrochloride (661 mg, 2.62 mmol), 1-hydroxy-7-azabenzotriazole (175 mg, 1.29 mmol), CH2Cl2 (30 mL), EDC (588 mg, 3.07 mmol) and stirring at room temp for 18 h, 781.5 mg (78%) of the title compound is isolated by filtration as a light pink solid. LC/MS (Condition A): ret. T=2.64 min, (M+H)+ 385. 1H NMR (500 MHz, methanol-d4) δ ppm 9.66 (1 H, s), 7.97 (1 H, s), 4.37-4.53 (1 H, m), 4.21-4.32 (1 H, m), 4.16 (2 H, d, J=0.92 Hz), 1.47 (9 H, s), 1.38 (6 H, dd, J=15.72, 7.17 Hz).

Sources & evidence

ORD record
ord-bbd4dce678bc435ea79366f2b95de631
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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