Diisopropylethylamine → (S)-methyl 2-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanamido)-3-(4-methoxyphenyl)propanoate

HRID 58918

Reaction equation

HRID 58918 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(OC([NH:53][C@@H:54]([CH2:59][C:60]1[CH:65]=[CH:64][C:63]([O:66][CH3:67])=[CH:62][CH:61]=1)[C:55]([O:57][CH3:58])=[O:56])=O)(C)(C)C.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:1]([O:8][CH2:9][C@H:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:11]([NH:53][C@@H:54]([CH2:59][C:60]1[CH:61]=[CH:62][C:63]([O:66][CH3:67])=[CH:64][CH:65]=1)[C:55]([O:57][CH3:58])=[O:56])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11220582(S)-2-Tert-butoxycarbonylamino-3-(4-methoxy-phenyl)-propionic acid methyl ester

Product 1

HCID 117690792(S)-methyl 2-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanamido)-3-(4-methoxyphenyl)propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid (1.00 g, 3.39 mmol) in DMF (10 mL) at 0° C. was added HATU (1.42 g, 3.73 mmol). The mixture was stirred for 5 min to dissolve the solids at which time (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl)propanoate (0.708 g, 3.39 mmol) and DIEA (1.77 mL, 10.2 mmol) was added. The reaction mixture was stirred at ambient temperature for 30 min then quenched with sodium bicarbonate (sat.), extracted with ethyl acetate (2×), dried with sodium sulfate, filtered, and concentrated to provide crude (S)-methyl 2-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanamido)-3-(4-methoxyphenyl)propanoate as a yellow oil that was carried forward without further purification. MS (EI) for C26H34N2O7, found 387.1 (M-Boc).

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at ambient temperature for 30 min
  3. customthen quenched with sodium bicarbonate (sat.)
  4. extractionextracted with ethyl acetate (2×)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fc9688e0467741d18efa5c72106a65cf
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Linked notes

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