1,2-Dichloroethane → HCID 86700114, compound

HRID 1755468Notes

Reaction equation

HRID 1755468 reaction equation
[NH2:1][C@@H:2]([CH3:22])[C:3]([NH:5][C@@H:6]([CH3:21])[C:7]([NH:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[S:15][C:16]([CH:19]=[O:20])=[CH:17][N:18]=1)=[O:8])=[O:4].[CH3:23][C@H:24]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:25](O)=[O:26].ON1C2N=CC=CC=2N=N1.CN1CCOCC1.C(Cl)CCl>C(Cl)Cl>[CH:19]([C:16]1[S:15][C:14]([NH:13][CH2:12][CH2:11][CH2:10][NH:9][C:7](=[O:8])[C@@H:6]([NH:5][C:3](=[O:4])[C@@H:2]([NH:1][C:25](=[O:26])[C@@H:24]([NH:28][C:29](=[O:30])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])[CH3:23])[CH3:22])[CH3:21])=[N:18][CH:17]=1)=[O:20]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 85082Tert-butoxycarbonylalanineHCID 181649HOAtHCID 89858313HCID 89858313, compound

Product 1

HCID 86700114HCID 86700114, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure as described in Example 24, except using the material from Example 72 (255 mg, 0.539 mmol), N-alpha-t-BOC-L-Alanine (117 mg, 0.620 mmol), 1-hydroxy-7-azabenzotriazole (36.7 mg, 0.269 mmol), CH2Cl2 (10 mL), N-methylmorpholine (250 μlit, 2.27 mmol), EDC (124 mg, 0.647 mmol), and stirring at room temp for 18 h, 215.3 mg (80%) of the title compound is obtained as a white solid. The desired product crystallized out of the reaction, is collected by vacuum filtration and dried under high vacuum for several hours. LC/MS (Condition A): ret. T=2.70 min, (M+H)+ 499.26. 1H NMR (500 MHz, methanol-d4) δ ppm 9.61 (1 H, d, J=2.14 Hz), 7.96 (1 H, d, J=2.14 Hz), 4.16-4.38 (2 H, m), 3.92-4.07 (1 H, m), 3.43 (2 H, t, J=6.26 Hz), 1.88 (2 H, t, J=5.95 Hz), 1.26-1.51 (18 H, m).

Sources & evidence

ORD record
ord-7c1e3f68ca7048938b92da14bcc5c575
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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