Water → HCID 131733371, compound

HRID 2271395Notes

Reaction equation

HRID 2271395 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:18]=[C:17](CC(O)=O)[CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[NH2:25][C@H:26]([C:28]([O:30][CH3:31])=[O:29])[CH3:27].C1CCC(N=C=N[CH:41]2[CH2:46]CCCC2)CC1.[OH2:47]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCCCCC.CCOC(C)=O>[CH3:31][O:30][C:28](=[O:29])[C:26]([NH:25][C:46](=[O:47])[CH3:41])([C:17]1[CH:16]=[CH:15][CH:14]=[C:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][C:5]3[CH:23]=[CH:24][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:12][CH:11]=2)[N:18]=1)[CH3:27]

Participants

9

Reactant 4

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 82335L-Alanine methyl esterHCID 66666572HCID 66666572, compound

Product 1

HCID 131733371HCID 131733371, compoundYield 81%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 25 (30 mg, 0.1 mol) in DCM (1 mL) was added (L)-Ala-OMe (10.3 mg, 0.1 mmol), DCC (23.7 mg, 0.12 mmol) and DMAP (1.2 mg, 0.01 mmol). The reaction mixture was stirred overnight at room temperature. After the reaction was complete, H2O (1 mL) was added. The organic phase was separated and dried over anhydrous Na2SO4. The solvent was removed and the residue was purified by the preparative TLC (MeOH:DCM=1:9, then EtOAc:Hexane=2:1) to give compound 26 (2 mg, 81% yield, LC/MS: m/z=409 [M+H]+, 1H NMR (400 MHz, CD3OD): δ 8.04 (d, J=8.8 Hz, 2H), 7.81 (t, J=7.8 Hz 1H), 7.7 (d, J=7.2 Hz, 1H), 7.31 (d, J=7.0 Hz, 1H), 7.03-7.1 (m, 6H), 4.47 (q, J=7.3 Hz, 1H), 3.83 (s, 2H), 3.71 (s, 3H), 1.42 (d, J=7.2 Hz, 3H)).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. customThe solvent was removed
  4. customthe residue was purified by the preparative TLC (MeOH

Sources & evidence

ORD record
ord-235e8e65a4be498b996a270a0934ffc6
Source dataset
uspto-grants-2015_09
Patent number
US09120752B2

Reaction notes

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