Ethyl Acetate → HCID 25073712, compound

HRID 1944192Notes

Reaction equation

HRID 1944192 reaction equation
CCO[C:4](C)=[O:5].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[CH2:21][N:20]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([N+]([O-])=O)[CH:29]=1)[CH2:19][CH2:18]2)C1C=CC=CC=1.[CH3:37][OH:38].[OH2:39]>>[OH:39][C:31]1[CH:30]=[C:29]2[C:28](=[CH:33][C:32]=1[O:38][CH3:37])[CH2:27][N:20]([CH2:19][C:18]1[CH:23]=[C:24]([O:25][CH3:26])[C:15]([O:14][CH3:7])=[CH:16][C:17]=1[O:5][CH3:4])[CH2:21][CH2:22]2

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 22242641Methanol--water (1/1)HCID 25071537HCID 25071537, compound

Product 1

HCID 25073712HCID 25073712, compound

Procedure

Yellow powder, 170 mg (48%), mp=152-153° C., Rf: 0.48 (EtOAc), 1H NMR (270 MHz, CDCl3) δ 2.67-2.79 (4H, m, 2×CH2), 3.57 (2H, s, CH2), 3.64 (2H, s, CH2), 3.80 (3H, s, CH3O), 3.81 (3H, s, CH3O), 3.82 (3H, s, CH3O), 3.89 (3H, s, CH3O), 5.61 (1H, br, OH), 6.46 (1H, s, ArH), 6.53 (1H, s, ArH), 6.62 (1H, s, ArH), 7.01 (1H, s, ArH), 13C NMR (67.5 MHz, CDCl3) δ 28.6 (CH2), 50.6 (CH2), 55.3 (CH2), 55.8 (CH2), 56.0 (CH3O), 56.2 (CH3O), 56.6 (CH3O), 56.8 (OCH3), 97.6 (CH(Ar)), 108.9 (CH(Ar)), 114.2 (CH(Ar)), 114.3 (CH(Ar)), 118.0 (C(Ar)), 126.4 (C(Ar)), 127.1 (C(Ar)), 143.1 (C(Ar)), 144.0 (C(Ar)), 144.9 (C(Ar)), 148.5 (C(Ar)) and 152.1 (C(Ar)). LC/MS (APCI−) tr=0.60 min m/z 358.21(M−H)−; MeOH/H2O 95/5; HPLC tr=2.41 min (98.2%). (CH3CN/H2O90/10)

Workup

  1. customtr=0.60 min m/z
  2. custom=2.41 min (98.2%)

Sources & evidence

ORD record
ord-df91d9eccf594c74bdc83ed0075d3af1
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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