1,2-Dichloroethane → (S)-4-((tert-Butoxycarbonyl)(5-formylthiazol-2-yl)amino)-2-((tert-butoxycarbonyl)amino)butanoic acid

HRID 1755491Notes

Reaction equation

HRID 1755491 reaction equation
[C:1]([O:5][C:6]([N:8]([C:24]1[S:25][C:26]([CH:29]=[O:30])=[CH:27][N:28]=1)[CH2:9][CH2:10][C@H:11]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:12]([O:14]C)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].ClCCCl.C[Sn](C)(C)O>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([C:24]1[S:25][C:26]([CH:29]=[O:30])=[CH:27][N:28]=1)[CH2:9][CH2:10][C@H:11]([NH:16][C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C:12]([OH:14])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 86700133(S)-Methyl 4-((tert-butoxycarbonyl)(5-formylthiazol-2-yl)amino)-2-((tert-butoxycarbonyl)amino)butanoateHCID 178477787HCID 178477787, compound

Product 1

HCID 86700134(S)-4-((tert-Butoxycarbonyl)(5-formylthiazol-2-yl)amino)-2-((tert-butoxycarbonyl)amino)butanoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
69 °C

Procedure

To a dry 2-5 mL microwave vial under N2 is added material from Example 116 (120 mg, 0.271 mmol) and anhydrous 1,2-dichloroethane (3 mL). The resulting solution is flushed with N2, treated with trimethylstannanol (60 mg, 0.332 mmol), securely capped and heated in a microwave heating unit at 60-78° C. for 6.5 h. The reaction is diluted with ethyl acetate (75 mL), and the organic layer is washed with 0.5N aqueous HCl (3×15 mL), brine (15 mL), dried over Na2SO4, filtered and evaporated to dryness to give 11 mg (95%) of the title compound as a pale yellow glass that contains 0.5 equivalents of the tin reagent. LC/MS (Condition A): ret. T=3.69 min, (M+Na) 452.

Workup

  1. customThe resulting solution is flushed with N2
  2. customsecurely capped
  3. temperatureheated in a microwave
  4. washthe organic layer is washed with 0.5N aqueous HCl (3×15 mL), brine (15 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-d0b39ee4953a488e81dc9dfc54425b0a
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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