1,2-Dichloroethane → tert-Butyl(S)-((S)-1-(3-(5-formylthiazol-2-ylamino)propylamino)-1-oxopropan-2-ylamino)-1-oxopropan-2-ylcarbamate

HRID 1755467Notes

Reaction equation

HRID 1755467 reaction equation
[NH2:1][C@@H:2]([CH3:17])[C:3]([NH:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[S:11][C:12]([CH:15]=[O:16])=[CH:13][N:14]=1)=[O:4].[CH3:18][C@H:19]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:20](O)=[O:21].ON1C2N=CC=CC=2N=N1.CN1CCOCC1.C(Cl)CCl>C(Cl)Cl>[CH:15]([C:12]1[S:11][C:10]([NH:9][CH2:8][CH2:7][CH2:6][NH:5][C:3](=[O:4])[C@@H:2]([NH:1][N:23]([C@@H:19]([CH3:18])[CH:20]=[O:21])[C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH3:17])=[N:14][CH:13]=1)=[O:16]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 85082Tert-butoxycarbonylalanineHCID 181649HOAtHCID 86700111(S)-2-Amino-N-(3-(5-formylthiazol-2-ylamino)propyl)propanamide

Product 1

HCID 89858180tert-Butyl(S)-((S)-1-(3-(5-formylthiazol-2-ylamino)propylamino)-1-oxopropan-2-ylamino)-1-oxopropan-2-ylcarbamateYield 66.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure as described in Example 24, except using the material from Example 70 (260 mg, 0.790 mmol), N-alpha-t-BOC-L-Alanine (161 mg, 0.853 mmol), 1-hydroxy-7-azabenzotriazole (53.7 mg, 0.395 mmol), CH2Cl2 (15 mL), N-methylmorpholine (178 μlit, 1.62 mmol), and EDC (182 mg, 0.948 mmol), 223.5 mg (66.2%) of the title compound is obtained as an off white solid. Purification is done by BIOTAGE® Silica gel chromatography on a 25 g Thompson Single Step silica cartridge using a linear gradient from 100% CH2Cl2 to 100% ACN over 10 column volumes, with a hold at 100% ACN for 15 column volumes. LC/MS (Condition A): ret. T=2.59 min, (M+H)+ 428.23.

Sources & evidence

ORD record
ord-5d8bd2d1f60c4c1aa80223c71a931bb9
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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