Propionic acid, 3-iodo-, methyl ester → HCID 89601716, compound

HRID 869067Notes

Reaction equation

HRID 869067 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[C:15]3[C:11](=[N:12][N:13]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])[C:14]=3[CH:24]([CH3:26])[CH3:25])[C:10]2=[O:35])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:36][O:37][C:38](=[O:42])[CH2:39][CH2:40]I>>[CH3:36][O:37][C:38](=[O:42])[CH2:39][CH2:40][C:16]1([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[C:15]2[C:11](=[N:12][N:13]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])[C:14]=2[CH:24]([CH3:26])[CH3:25])[C:10](=[O:35])[N:9]1[C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1

Participants

3

Reactant 2

HCID 138407Propionic acid, 3-iodo-, methyl esterHCID 89601326HCID 89601326, compound

Product 1

HCID 89601716HCID 89601716, compound

Procedure

The title compound was prepared in analogy to the procedure described for example 74 but using the compound prepared in example 88 and 2 equivalents of 3-iodo-propionic acid methyl ester (Scapens, D.; Adams, H.; Johnson, T. R.; Mann, B. E.; Sawle, P.; Aqil, R.; Perrior, T.; Motterlini, R. Dalton Transactions 2007, 43, 4962-4973). The reaction mixture was stirred for 2 h at rt. The crude material was purified by silica gel column chromatography (heptane/ethyl acetate, 1:0→7:3→2:3) followed by preparative HPLC (Column: XBridge, 30×100 mm. Flow: 30 mL/min. Gradient: 30% to 60% B in 15 min, 60% B for 5 min, 60% to 90% B in 5 min; A=0.1% TFA in water, B=0.1% TFA in acetonitrile). tR: 1.42 min (LC-MS 3); ESI-MS: 596.3 [M+H]+ (LC-MS 3).

Workup

  1. customThe crude material was purified by silica gel column chromatography (heptane/ethyl acetate, 1:0→7:3→2:3)
  2. waitGradient: 30% to 60% B in 15 min
  3. wait60% B for 5 min
  4. wait60% to 90% B in 5 min

Sources & evidence

ORD record
ord-e2ba9b2f77194910a5bc26f3a32978cd
Source dataset
uspto-grants-2015_03
Patent number
US08969341B2

Reaction notes

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