Formic Acid → HCID 10119223, compound

HRID 1006257Notes

Reaction equation

HRID 1006257 reaction equation
C(O)=O.C([O:8][C:9](=[O:46])[CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=1)[C:16]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:15]2[C:35]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH:43]2[CH2:45][CH2:44]2)=[CH:37][CH:36]=1)(C)(C)C>ClCCl>[CH:43]1([CH2:42][O:41][C:38]2[CH:37]=[CH:36][C:35]([C:15]3[C:14]4[C:18](=[CH:19][CH:20]=[C:12]([O:11][CH2:10][C:9]([OH:46])=[O:8])[CH:13]=4)[N:17]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=4)[C:16]=3[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:40][CH:39]=2)[CH2:44][CH2:45]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 22676737HCID 22676737, compound

Product 1

HCID 10119223HCID 10119223, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Formic acid (1 mL) was added to a stirred solution of ethyl 5-(2-tert-butoxy-2-oxoethoxy)-3-[4-(cyclopropylmethoxy)phenyl]-1-(3-methoxybenzyl)-1H-indole-2-carboxylate (Example 150, 20 mg, 0.035 mmol) in dichloromethane (1 mL). The reaction was stirred for 1 h and then concentrated in vacuo. Flash chromatography of the residue over silica gel using (1:1 ethyl acetate/hexane) gave 10 mg (53% of the desired product. The product had: 1H NMR (300 MHz, CD3OD) δ 7.30-7.48 (m, 3 H), 6.92-7.19 (m, 4 H), 6.77 (dd, 1 H), 6.54-6.68 (m, 3 H), 5.79 (s, 2 H), 4.61 (s, 2 H), 4.13 (q, 2 H), 3.95 (d, 2 H), 3.74 (s, 3 H), 1.29-1.41 (m, 1 H), 1.25 (t, 3 H), 0.61-0.71 (m, 2 H), 0.39-0.49 (m, 2 H); mass spectroscopy gave MH+ of 530.2 (calc'd exact mass for C31H31NO7=529.21).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82e281222f1e46ca8fe6e052cd84c837
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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