Diisopropylethylamine → HCID 73196385, compound

HRID 1953911Notes

Reaction equation

HRID 1953911 reaction equation
[C:1]([NH:5][C:6](=[O:24])[C@H:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)[NH2:8])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH:34]1([N:40]([CH3:49])[C@H:41]([C:46](O)=[O:47])[CH2:42][CH:43]([CH3:45])[CH3:44])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH2:17]([O:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][CH:7]([NH:8][C:46](=[O:47])[CH:41]([N:40]([CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)[CH3:49])[CH2:42][CH:43]([CH3:45])[CH3:44])[C:6](=[O:24])[NH:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:15][CH:14]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11401906HCID 11401906, compoundHCID 15517727(S)-2-amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamide

Product 1

HCID 73196385HCID 73196385, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

O-Benzyl-L-tyrosine-t-butyl-amide (Ia, 0.5 g, 1.53 mmol) was dissolved in DMF (8 mL) and treated with diisopropylethylamine (0.8 mL, 4.6 mmol), N-cyclohexyl-N-methyl-leucine (Iid, 0.34 g, 1.53 mmol), and HBTU (0.58 g, 1.53 mmol). The reaction was stirred for 2 hours, then diluted with EtOAc (100 mL), washed with saturated bicarbonate solution (2×100 mL), brine (100 mL), dried over Na2SO4, and concentrated. The residue was chromatographed on silica gel eluting with 50% EtOAC/hexane. The resulting material was chromatographed again on silica gel eluting with 8% acetone/CH2Cl2 to give 0.11 g (14%) of the title compound. MS: 537 (M+1 for C33H49N3O3); TLC: SiO2, Rf 0.57 (10% MeOH/CH2Cl2).

Workup

  1. washwashed with saturated bicarbonate solution (2×100 mL), brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel eluting with 50% EtOAC/hexane
  5. customThe resulting material was chromatographed again on silica gel eluting with 8% acetone/CH2Cl2

Sources & evidence

ORD record
ord-8d0d7bb5911844e093ff55da787c039f
Source dataset
uspto-grants-2000_09
Patent number
US06117841

Reaction notes

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