Diisopropylethylamine → HCID 131737024, compound

HRID 58902Notes

Reaction equation

HRID 58902 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:22][C@@H:23]([CH2:30][C:31]1[CH2:35][CH2:34][CH2:33][CH:32]=1)[C:24]([C@@:26]1([CH3:29])[CH2:28][O:27]1)=[O:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:31]1([CH2:30][C@H:23]([NH:22][C:10](=[O:12])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:24]([C@@:26]2([CH3:29])[CH2:28][O:27]2)=[O:25])[CH2:35][CH2:34][CH2:33][CH:32]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2762280Boc-O-methyl-L-tyrosineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117607719HCID 117607719, compound

Product 1

HCID 131737024HCID 131737024, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (S)-2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl)propanoic acid (2.00 g, 6.78 mmol) and (S)-2-amino-3-(cyclopent-1-en-1-yl)-1-((R)-2-methyloxiran-2-yl)propan-1-one (1.98 g, 6.78 mmol) in DMF (10 mL) at 0° C. was added HATU (3.00 g, 8.36 mmol) followed by DIEA (5.90 mL, 33.9 mmol) and the mixture was stirred for 15 min then quenched with NaHCO3 (sat., aq.), extracted with EtOAc (2×), washed with brine, dried with sodium sulfate, filtered, and concentrated. Purification by column chromatography (1:1 hexanes/EtOAc) provided tert-butyl ((S)-1-(((S)-3-(cyclopent-1-en-1-yl)-1-((R)-2-methyloxiran-2-yl)-1-oxopropan-2-yl)amino)-3-(4-methoxyphenyl)-1-oxopropan-2-yl)carbamate (2.62 g, 82%) as a colorless oil. MS(EI) for C26H36N2O6, found 473.3 (MH)+.

Workup

  1. customthen quenched with NaHCO3 (sat., aq.)
  2. extractionextracted with EtOAc (2×)
  3. washwashed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-f6d3be7e6f2041fbae717d9845d73ebe
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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