HCID 87232360, compound → HCID 130283708, compound

HRID 885706Notes

Reaction equation

HRID 885706 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([NH:31]C(=O)OC(C)(C)C)[C:17]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27](=[O:30])[NH:28][OH:29])=[CH:23][CH:22]=2)=[O:18])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:31][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][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([NH:28][OH:29])=[O:30])=[CH:25][CH:26]=1)=[O:18]

Participants

3

Reactant 1

HCID 87232360HCID 87232360, compound

Product 1

HCID 130283708HCID 130283708, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

t-Butyl 3-(5-(benzyloxy)pyridin-2-yl)-1-(4-(hydroxyl-carbamoyl)benzylamino)-1-oxopropan-2-ylcarbamate (0.26 g, 0.5 mmol) was dissolved in TFA/DCM (v/v=1:1) (30 mL) and stirred for 4 h at room temperature (monitored by TLC). The solution was evaporated with DCM three times to give 0.021 g HPW101x048 (81%): mp 151-154° C.; NMR (400 MHz in CDCl3, Bruker AVANCE-400): δ 3.12 (m, 2H, CH2), 4.25 (m, 2H, CH2), 4.40 (m, 1H, CH), 5.15 (s, 1H, OBn), 7.21 (m, 3H, Ar—H), 7.40 (m, 7H, Ar—H), 7.67 (d, 1H, Ar—H, J=8.21 Hz), 7.84 (d, 1H, Ar—H, J=7.96 Hz), 8.26 (br, 2H, NH2), 8.27 (s, 1H, NH), 8.92 (br, 1H, NH), 11.19 (br, 1H, OH).

Workup

  1. customThe solution was evaporated with DCM three times
  2. customto give 0.021 g

Sources & evidence

ORD record
ord-c36a9e488ad34265810e04efe508fb52
Source dataset
uspto-grants-2012_08
Patent number
US08242282B2

Reaction notes

Loading…