1-(Benzyloxy)-4-iodobenzene → HCID 59164833, compound

HRID 2264805Notes

Reaction equation

HRID 2264805 reaction equation
[O:1]=[C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:4][CH2:3]1.[C:19]1([CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30](I)=[CH:29][CH:28]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH3:11][C:10]([O:9][C:7]([NH:6][C@H:5]([CH2:4][CH2:3][C:2](=[O:1])[C:30]1[CH:31]=[CH:32][C:27]([O:26][CH2:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:28][CH:29]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:8])([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 5196711-(Benzyloxy)-4-iodobenzeneHCID 8208851-Boc-D-Pyroglutamic acid ethyl ester

Product 1

HCID 59164833HCID 59164833, compound

Procedure

The title compound was synthesized (2.9 g, 16%) following a similar procedure as set out earlier in Description 6 starting from 1-(1,1-dimethylethyl) 2-ethyl (2R)-5-oxo-1,2-pyrrolidinedicarboxylate (D32, 10.5 g 40.8 mmol) and 4-iodophenyl phenylmethyl ether (13.34 g, 43 mmol); Rt (HPLC): 6.37 min; MS: (ES/+) 464 m/z: [M+Na+], C25H31NO6 requires 441; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.92 (d, 2H); 7.29-7.45 (m, 5H); 6.99 (d, 2H); 5.18 (bs, 1H); 5.12 (s, 2H); 4.29-4.4 (bm, 1H); 4.20 (q, 2H); 2.94-3.16 (m, 2H); 2.22-2.33 (m, 1H); 2.00-2.15 (m, 1H); 1.39 (s, 9H); 1.28 (t, 3H).

Sources & evidence

ORD record
ord-fe37b006ce1f484b80fefeba5ca3f36e
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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