HCID 11568581, compound → HCID 11548651, compound

HRID 1018348Notes

Reaction equation

C(O[C:9]([C:11]1[N:12]=[C:13]([CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[NH:14][C:15]=1[CH2:16][O:17][C:18]12[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2)=[O:10])C1C=CC=CC=1.[CH2:34]([O:41][C:42](=[O:50])[C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([NH2:49])[CH:44]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[CH2:34]([O:41][C:42](=[O:50])[C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([NH:49][C:9]([C:11]2[N:12]=[C:13]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[NH:14][C:15]=2[CH2:16][O:17][C:18]23[CH2:27][CH:22]4[CH2:21][CH:20]([CH2:26][CH:24]([CH2:23]4)[CH2:25]2)[CH2:19]3)=[O:10])[CH:44]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

Reactant 2

HCID 11568581HCID 11568581, compound

HCID 15428374Benzyl 3-aminobenzoate

Product 1

HCID 11548651HCID 11548651, compoundYield 65.5%

Procedure

The product of step d (0.76 g, 2.122 mmol) was reacted with 3-amino-benzoic acid benzyl ester (0.48 g, 2.12 mmol) according to the procedure of Example 20, step d. The crude material was purified by flash chromatography (silica, DCM/ethyl acetate 98:2, then 95:5) to afford colourless foam (786 mg, 65.5%). 1H NMR (300 MHz, CDCl3) 9.50 and 8.90 (1H, 2× br s), 8.15 (2H, m), 7.81 (1H, d), 7.40 (6H, m), 5.38 (2H, s), 4.98 (2H, br s), 2.71 (1H, m), 2.16 (3H, br s), 2.00 (2H, m), 1.85-1.24 (20H, m).

Workup

customThe crude material was purified by flash chromatography (silica, DCM/ethyl acetate 98:2

Sources & evidence

ORD record: ord-81354ccb96f848dfa25bf78c8de5bf07
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479531B1

Reaction notes

Loading…