1,2-Dichloroethane → HCID 53783522, compound

HRID 751456Notes

Reaction equation

HRID 751456 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C:19](=[O:26])[C@@H:20]([NH2:25])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH:13]([OH:27])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[O:42]1[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=2[CH:44]=[C:43]1[C:51](O)=[O:52]>ClCCl.CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C:19](=[O:26])[C@@H:20]([NH:25][C:51]([C:43]2[O:42][C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=3[CH:44]=2)=[O:52])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH:13]([OH:27])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 10331Benzofuran-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 53929954HCID 53929954, compound

Product 1

HCID 53783522HCID 53783522, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-((S)-2-amino-4-methyl-pentanoylamino)-3-hydroxy-azepane-1-carboxylic acid benzyl ester of Example 78a (3.2 g) in dichloromethane (200 mL) was added EDC (1.48 g), HOBt (1.05 g), TEA (1.29 mL) and benzofuran-2-carboxylic acid. The reaction was stirred until complete. Workup and column chromatography (2% methanol:dichloromethane) provided the title compound (3.78 g): MS(EI) 521 (M+H+).

Sources & evidence

ORD record
ord-9e289e2ab540490eae86f205caa1e624
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

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