Diisopropylethylamine → HCID 68725930, compound

HRID 2381027Notes

Reaction equation

HRID 2381027 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:17]([OH:19])=O)=[CH:11][C:10]=1[OH:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:54][C:55]([CH3:61])([CH3:60])[C:56]([O:58][CH3:59])=[O:57].C(N(CC)C(C)C)(C)C>CC(N(C)C)=O.O.C(OCC)(=O)C>[CH3:59][O:58][C:56](=[O:57])[C:55]([NH:54][C:17](=[O:19])[C@@H:16]([NH:20][C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([OH:28])[CH:11]=1)([CH3:61])[CH3:60]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10524262HCID 10524262, compoundHCID 13258034Methyl 2-aminoisobutyrate hydrochloride

Product 1

HCID 68725930HCID 68725930, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

(S)-3-(4-benzyloxy-3-hydroxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid (465 mg) was dissolved in anhydrous DMA (5 ml) and HBTU (910 mg) added in portions followed by methyl 2-aminoisobutyrate hydrochloride (366 mg). N,N-Diisopropylethylamine (0.4 ml) was added and the solution stirred at room temperature for 3 days. The mixture was diluted with water and ethyl acetate. The aqueous phase was extracted with ethyl acetate and the combined organic extracts were washed with dil HCl, with aq sodium bicarbonate with water and with brine. Drying (MgSO4) and evaporation of solvent gave the crude 2-[(S)-3-(4-benzyloxy-3-hydroxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-2-methyl-propionic acid methyl ester as a gum, 690 mg; HPLC/MS retention time 5.77 min, m/z 487.

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. washthe combined organic extracts were washed with dil HCl, with aq sodium bicarbonate with water and with brine
  3. customDrying
  4. custom(MgSO4) and evaporation of solvent

Sources & evidence

ORD record
ord-310f12fc3c85401493ef5fdebe2773d5
Source dataset
uspto-grants-2012_09
Patent number
US08258097B2

Reaction notes

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