(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(2-((5-formylthiazol-2-yl)amino)acetamido)propanoate → (S)-2-((tert-Butoxycarbonyl)amino)-3-(2-((5-formylthiazol-2-yl)amino)acetamido)propanoic acid

HRID 1755492Notes

Reaction equation

HRID 1755492 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][NH:15][C:16](=[O:26])[CH2:17][NH:18][C:19]1[S:20][C:21]([CH:24]=[O:25])=[CH:22][N:23]=1)[C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Sn](C)(C)O>ClCCCl>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][NH:15][C:16](=[O:26])[CH2:17][NH:18][C:19]1[S:20][C:21]([CH:24]=[O:25])=[CH:22][N:23]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 86700128(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(2-((5-formylthiazol-2-yl)amino)acetamido)propanoateHCID 178477787HCID 178477787, compound

Product 1

HCID 86700135(S)-2-((tert-Butoxycarbonyl)amino)-3-(2-((5-formylthiazol-2-yl)amino)acetamido)propanoic acidYield 43%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

Following the general procedure as described in Example 117, except using material from Example 106 (100 mg, 0.259 mmol), 1,2-dichloroethane (2.5 mL), trimethylstannanol (140 mg, 0.0.776 mmol), and heating in a microwave for 2.5 h at 80° C. under normal power, 41.4 mg (43%) of the title compound is isolated as a thick oil that contains 0.25 equivalents of the tin reagent. LC/MS (Condition A): ret. T=2.28 min, (M+H)+ 373.

Sources & evidence

ORD record
ord-bfb4a83fac614020871ac0446e7949f6
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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