Dichloromethane → HCID 178434958, compound

HRID 535203Notes

Reaction equation

HRID 535203 reaction equation
C(OC([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])=O)(C)(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(Cl)Cl.[CH3:40][C:41]1[O:45][C:44](=[O:46])[O:43][C:42]=1[CH2:47][O:48][C:49](=[O:77])[C@@:50]([CH2:75]O)([CH3:74])[CH2:51][C@H:52]([NH:66][C:67]([C:69]1[NH:70][N:71]=[N:72][CH:73]=1)=[O:68])[CH2:53][C:54]1[CH:59]=[CH:58][C:57]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)=[CH:56][CH:55]=1.CN1CCOCC1>>[CH3:40][C:41]1[O:45][C:44](=[O:46])[O:43][C:42]=1[CH2:47][O:48][C:49](=[O:77])[C@@:50]([CH2:75][O:15][C:13](=[O:14])[C@@H:9]([NH2:8])[CH:10]([CH3:11])[CH3:12])([CH3:74])[CH2:51][C@H:52]([NH:66][C:67]([C:69]1[NH:70][N:71]=[N:72][CH:73]=1)=[O:68])[CH2:53][C:54]1[CH:55]=[CH:56][C:57]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)=[CH:58][CH:59]=1

Participants

7

Reactant 6

HCID 6344DichloromethaneHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 83693Boc-L-ValineHCID 178434957HCID 178434957, compound

Product 1

HCID 178434958HCID 178434958, compoundYield 33.8%

Procedure

N-(t-Butoxycarbonyl)-L-valine (75 mg, 340 μmol), HOBt (47 mg, 0.34 mmol), EDCI (0.061 mL, 0.34 mmol), and DCM (1.8 mL, 29 mmol) were combined and stirred for 15 minutes. (2S,4R)-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-4-[(3H-[1,2,3]triazole-4-carbonyl)-amino]-pentanoic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester (150 mg, 290 μmol) and 4-methylmorpholine (38 μL, 340 μmol) were added, and the resulting mixture was stirred at room temperature for 3 hours, then evaporated. The crude material was purified by reverse phase column ((Interchim reverse phase chromatography column) to yield the title compound (60.8 mg; purity 98%) as a white solid. MS m/z [M+H]+ calc'd for C32H37N5O8, 620.26. found 620.3.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 3 hours
  2. customevaporated
  3. customThe crude material was purified by reverse phase column ((Interchim reverse phase chromatography column)

Sources & evidence

ORD record
ord-c323548525ca435cb4101aebdd793774
Source dataset
uspto-grants-2014_10
Patent number
US08853427B2

Reaction notes

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