HCID 76155194, compound → HCID 76155193, compound

HRID 885704Notes

Reaction equation

HRID 885704 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([NH:33]C(=O)OC(C)(C)C)[C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][C:29]([NH:31][OH:32])=[O:30])=[CH:22][CH:21]=2)=[O:18])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:33][CH:16]([CH2:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][N:13]=1)[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][C:29]([NH:31][OH:32])=[O:30])=[CH:22][CH:21]=1)=[O:18]

Participants

3

Reactant 1

HCID 76155194HCID 76155194, compound

Product 1

HCID 76155193HCID 76155193, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

t-Butyl 3-(5-(benzyloxy)pyridin-2-yl)-1-(4-(4-(hydroxyamino)-4-oxobutyl)-phenylamino)-1-oxopropan-2-ylcarbamate (0.1 g, 0.19 mmol) was dissolved in DCM/TFA (v/v=1:1) (30 mL), and stirred at room temperature for 4 h (monitored by TLC). The solution was evaporated in vacuo to give Compound 5 (0.062 g, 61%). mp>300° C.; NMR (400 MHz in CDCl3, Bruker AVANCE-400): δ 1.75 (m, 2H, CH2), 1.95 (t, 2H, CH2, J=7.37 Hz), 2.52 (t, 2H, CH2, J=7.55 Hz), 3.16 (m, 2H, CH2), 4.30 (m, 1H, CH), 5.16 (s, 2H, OBn), 7.13 (d, 2H, Ar—H, J=8.06 Hz), 7.24 (d, 1H, Ar—H, J=8.47 Hz), 7.33-8.46 (m, 9H, Ar—H), 8.22 (br, 2H, NH2), 8.30 (m, 1H, NH), 8.64 (br, 1H, NH), 10.33 (br, 1H, OH), 10.36 (br, 1H, TFA).

Workup

  1. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-eaa3ae7c11054c109abdea67b396a9ce
Source dataset
uspto-grants-2012_08
Patent number
US08242282B2

Reaction notes

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