Formic Acid → HCID 14218637, compound

HRID 2107847Notes

Reaction equation

HRID 2107847 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:38]/[O:39]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)/[C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:21]([O:23][CH:24]([O:26][C:27]([O:29][CH:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[O:28])[CH3:25])=[O:22])=[C:15](/[CH:18]=[CH:19]\[CH3:20])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C(O)=O.[OH-].[Na+]>CCOC(C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:38]/[OH:39])/[C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:21]([O:23][CH:24]([O:26][C:27]([O:29][CH:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[O:28])[CH3:25])=[O:22])=[C:15](/[CH:18]=[CH:19]\[CH3:20])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 88605383HCID 88605383, compound

Product 1

HCID 14218637HCID 14218637, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product of Procedure 13 (62.7 g, 0.076 mol) and 90% aqueous formic acid (110 ml) was stirred at room temperature for 1 hr. The reaction mixture was diluted with EtOAc (600 ml) and ice-water (300 ml) and the lower layer was adjusted to pH 3.3 with 30% aq. NaOH under vigorous stirring. The upper layer was diluted to 2 L, separated, washed with water (500 ml×3) and brine, dried over MgSO4 and concentrated under diminished pressure. The residue was dissolved in toluene (300 ml) which was carefully transferred to the top surface of a silica gel column (Wakogel C-200, 800 g). The column was eluted with CH2Cl2, 0.5%, 1.0%, 1.5%, 2.0% and 3.0% MeOH in CH2Cl2, successively. The fractions which exhibited approximately Rf: 0.12 on TLC (SiO2, 5% MeOH-CH were combined and concentrated in vacuo to give 30.0 g (68%) of the desired product as an amorphous powder. The starting material was recovered (8.4 g, 14%) from the fractions which showed Rf 0.55 on TLC.

Workup

  1. additionThe upper layer was diluted to 2 L
  2. customseparated
  3. washwashed with water (500 ml×3) and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under diminished pressure
  6. dissolutionThe residue was dissolved in toluene (300 ml) which
  7. washThe column was eluted with CH2Cl2, 0.5%, 1.0%, 1.5%, 2.0% and 3.0% MeOH in CH2Cl2
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be513097e7db492992cd1893e15ae97a
Source dataset
uspto-grants-1990_06
Patent number
US04935508

Reaction notes

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