Thioglycolic Acid → HCID 178502865, compound

HRID 1024804Notes

Reaction equation

HRID 1024804 reaction equation
C([N:3](CC)CC)C.[C:8]([O:12][C:13](=[O:48])[NH:14][CH:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:47])[C:23]2[CH:28]=[C:27]([O:29][C:30]3[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=3)[CH:26]=[C:25]([O:38][C:39]3[CH:44]=[CH:43][C:42]([C:45]#[N:46])=[CH:41][CH:40]=3)[CH:24]=2)[CH2:17][CH2:16]1)([CH3:11])([CH3:10])[CH3:9].Cl.[CH3:50][O:51][NH2:52].SC[C:55]([OH:57])=O>C(O)C>[C:8]([O:12][C:13](=[O:48])[NH:14][CH:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:47])[C:23]2[CH:24]=[C:25]([O:38][C:39]3[CH:44]=[CH:43][C:42]([C:45](=[NH:46])[NH:52][O:51][CH3:50])=[CH:41][CH:40]=3)[CH:26]=[C:27]([O:29][C:30]3[CH:35]=[CH:34][C:33]([C:36](=[NH:3])[NH:37][O:57][CH3:55])=[CH:32][CH:31]=3)[CH:28]=2)[CH2:17][CH2:16]1)([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 1133Thioglycolic AcidHCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 66818598HCID 66818598, compound

Product 1

HCID 178502865HCID 178502865, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Triethylamine (2.5 ml, 1.81 mmol) was added to the suspension of {4-[3,5-bis-(4-cyano-phenoxy)-benzoylamino]-cyclohexyl}-carbamic acid tert-butyl ester (1.0 g, 1.81 mmol) in 15 ml of ethanol at 55° C. O-methyl-hydroxylamine hydrochloride solution (0.91 g in 3 ml of water (30% w/w)) and mercaptoacetic acid (0.51 ml, 7.24 mmol) were added to the reaction mixture at 55° C. under inert nitrogen atmosphere. Reaction mixture was stirred under nitrogen atmosphere at 90° C. for 40 h. After reaction completion, solvent was removed under vacuo and the residue was poured into ice-water to obtain white solid product which was filtered off and washed with water and hexane to afford 0.7 g of the required product. Percentage purity (LCMS): 69.3%, (M+1)=646+1.

Workup

  1. customReaction mixture
  2. customAfter reaction completion, solvent
  3. customwas removed under vacuo
  4. additionthe residue was poured into ice-water
  5. customto obtain white solid product which
  6. filtrationwas filtered off
  7. washwashed with water and hexane

Sources & evidence

ORD record
ord-90015f82fbfe4d0a8255302fce185bfa
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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