Diisopropylethylamine → HCID 69927875, compound

HRID 1582740Notes

Reaction equation

HRID 1582740 reaction equation
[C:1]([N:8]([CH3:28])[C@H:9]([C:25](O)=[O:26])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[C:30]1([C:36]2([CH2:40][NH2:41])[CH2:39][CH2:38][CH2:37]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:4]([O:3][C:1](=[O:2])[N:8]([C@H:9]([C:25](=[O:26])[NH:41][CH2:40][C:36]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:37][CH2:38][CH2:39]1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:13][CH:12]=1)[CH3:28])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 7010604N-[(1,1-Dimethylethoxy)carbonyl]-N-methyl-O-(phenylmethyl)-L-tyrosineHCID 22717871HCID 22717871, compound

Product 1

HCID 69927875HCID 69927875, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of Boc-NMe-Tyr(OBn)-OH (0.90 g, 2.3 mmol) and C-(1-phenyl-cyclobutyl)-methylamine hydrochloride (synthesized according to the method in Bridges, A. J., Hamilton, H. W., Moos, W. H., Szotek, D. L., N6−substituted Adenosines, U.S. Pat. No. 4,755,594) (0.46 g, 2.3 mmol) and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) (0.97 g, 5.6 mmol) in methylene chloride (10 mL) was treated with DIEA (0.86 mL, 5.1 mmol). The suspension was stirred at room temperature overnight. The resulting solution was concentrated. The residue was taken up in ethyl acetate. The solution was washed with 0.5 M HCl, saturated NaHCO3, dried over MgSO4, filtered, and concentrated. The oil was chromatographed (CH2Cl2:CH3OH 50:1) to give the desired product (1.07 g, 2.02 mmol; 87% yield). MS-APCI 529 (m+1).

Workup

  1. customsynthesized
  2. concentrationThe resulting solution was concentrated
  3. washThe solution was washed with 0.5 M HCl, saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe oil was chromatographed (CH2Cl2:CH3OH 50:1)

Sources & evidence

ORD record
ord-753801ab77c249268b428bf221a7a84c
Source dataset
uspto-grants-2004_05
Patent number
US06737410B1

Reaction notes

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