Water → HCID 178504137, compound

HRID 512917Notes

Reaction equation

HRID 512917 reaction equation
ClC[C:3]([NH:5][CH:6]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21](/[CH:25]=[CH:26]/[C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][C:31]([Cl:37])=[CH:32][CH:33]=3)[N:28]=2)[CH:20]=1)[CH2:7][CH2:8][C:9]1C=[CH:13][CH:12]=[CH:11][C:10]=1C(O)(C)C)=[O:4].[SH:38][CH2:39]C(O)=O.[CH3:43][C:44]([CH3:47])([O-:46])[CH3:45].[K+].[OH2:49].[O:50]1[CH2:54][CH2:53][CH2:52]C1>C(OC(=O)C)C.C(O)(=O)C>[Cl:37][C:31]1[CH:30]=[C:29]2[C:34]([CH:35]=[CH:36][C:27](/[CH:26]=[CH:25]/[C:21]3[CH:20]=[C:19]([CH:6]([NH:5][C:3]([SH:38]([CH3:39])[CH2:52][CH2:53][C:54]([OH:50])=[O:49])=[O:4])[CH2:7][CH2:8][C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:43]=4[C:44]([OH:46])([CH3:47])[CH3:45])[CH:24]=[CH:23][CH:22]=3)=[N:28]2)=[CH:33][CH:32]=1

Participants

8

Reactant 5

HCID 962WaterHCID 1133Thioglycolic AcidHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 86720730HCID 86720730, compound

Product 1

HCID 178504137HCID 178504137, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

(Ia.64): To a stirred solution of chloro-amide 28a (0.5 g, 0.93 mmol) in tetrahydrofuran (20 ml) kept under nitrogen was added 2-mercaptoaceticacid (0.130 g, 1.87 mmol) and potassium tert-butoxide (0.210 g, 1.87 mmol). The reaction mass was stirred for 5 hours, poured into water (100 ml) and acidified with glacial acetic acid (10 ml) followed by usual workup in ethylacetate and evaporation to give the residue. The resulted residue was purified by FC followed by trituration with hexane to afford (Ia.64) (0.2 g, 36%) as a pale yellow solid.

Workup

  1. customevaporation
  2. customto give the residue
  3. customThe resulted residue was purified by FC
  4. customto afford (Ia.64) (0.2 g, 36%) as a pale yellow solid

Sources & evidence

ORD record
ord-3ea29ba03f8d4229b9b512e5ef5a233b
Source dataset
uspto-grants-2015_08
Patent number
US09102665B2

Reaction notes

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