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

HRID 1755465Notes

Reaction equation

HRID 1755465 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[S:7][C:8]([CH:11]=[O:12])=[CH:9][N:10]=1.[CH3:13][C@H:14]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:15](O)=[O:16].ON1C2N=CC=CC=2N=N1.CN1CCOCC1.C(Cl)CCl>C(Cl)Cl>[CH:11]([C:8]1[S:7][C:6]([NH:5][CH2:4][CH2:3][CH2:2][NH:1][C:15](=[O:16])[C@@H:14]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH3:13])=[N:10][CH:9]=1)=[O:12]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 85082Tert-butoxycarbonylalanineHCID 181649HOAtHCID 867001102-(3-Aminopropylamino)thiazole-5-carbaldehyde

Product 1

HCID 86700112(S)-tert-Butyl 1-(3-(5-formylthiazol-2-ylamino)propylamino)-1-oxopropan-2-ylcarbamateYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure as described in Example 24, except using the material from Example 68 (254 mg, 0.984 mmol), N-alpha-t-BOC-L-Alanine (201 mg, 1.06 mmol), 1-hydroxy-7-azabenzotriazole (70.0 mg, 0.514 mmol), CH2Cl2 (15 mL), N-methylmorpholine (224 μlit, 2.04 mmol), and EDC (229 mg, 1.21 mmol), and stirring at room temp for 45 min., 267.3 mg (76%) of the title compound is obtained as a yellow 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% EtOAc, over 8.5 column volumes, with a hold at 100% EtOAc for 15 column volumes. LC/MS (Condition A): ret. T=2.54 min, (M+H)+ 357.20.

Sources & evidence

ORD record
ord-a25471c71ef549139f256a2de1904c57
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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