1,2-Dichloroethane → HCID 89867046, compound

HRID 1755476Notes

Reaction equation

HRID 1755476 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:20](O)=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:43]([O:46][C:47](=[O:54])[C@H:48]([CH2:50][CH:51]([CH3:53])[CH3:52])[NH2:49])[CH:44]=[CH2:45].ON1C2N=CC=CC=2N=N1.CN1CCOCC1.C(Cl)CCl>C(Cl)Cl>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:20]([NH:49][C@@H:48]([CH2:50][CH:51]([CH3:52])[CH3:53])[C:47]([O:46][CH2:43][CH:44]=[CH2:45])=[O:54])=[O:21])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 160716924-Methylbenzene-1-sulfonic acid--prop-2-en-1-yl L-leucinate (1/1)HCID 170401273-{[tert-Butoxy(hydroxy)methylidene]amino}-N-{[(9H-fluoren-9-yl)methoxy](hydroxy)methylidene}alanine

Product 1

HCID 89867046HCID 89867046, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure as described in Example 24, except using suspension of (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tert-butoxycarbonylamino)propanoic acid (500 mg, 1.172 mmol), L-leucine allyl ester p-toluenesulfonate salt (411 mg, 1.196 mmol), 1-hydroxy-7-azabenzotriazole (80 mg, 0.586 mmol), CH2Cl2 (40 mL), N-methylmorpholine (0.258 mL, 2.345 mmol), and EDC (247 ing, 1.290 mmol), 137 mg (20.16%) of the title compound is isolated as a white solid. Purification is done by BIOTAGE® Silica gel chromatography on a 90 g Thompson Single Step silica cartridge using a linear gradient from 100% Hexanes to 100% (1:1 EtOAc/Hexanes) over 12 column volumes. LC/MS (Condition A): ret. T=4.50 min, (2M+Na) 1181.97.

Sources & evidence

ORD record
ord-4f901d7cacfa4e9083258f7586cbe6cf
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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