(2S)-2-Amino-3-(4-(2-methoxycarbonyl-ethyl)-benzoylamino)-propionic acid tert-butyl ester → (1,1-dimethyl ethyl) N-(5-bromo-2-benzoxazolyl)-3-[[4-(3-methoxy-3-oxo-propyl)benzoyl]amino]-L-alaninate

HRID 1759716Notes

Reaction equation

HRID 1759716 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[CH:24]=[CH:23][C:9]([C:10]([NH:12][CH2:13][C@@H:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[NH2:15])=[O:11])=[CH:8][CH:7]=1.[Br:26][C:27]1[CH:28]=[CH:29][C:30]2[O:34][C:33](SC)=[N:32][C:31]=2[CH:37]=1>[Hg](OC(C)=O)OC(C)=O>[Br:26][C:27]1[CH:28]=[CH:29][C:30]2[O:34][C:33]([NH:15][C@H:14]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:13][NH:12][C:10](=[O:11])[C:9]3[CH:23]=[CH:24][C:6]([CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:25])=[CH:7][CH:8]=3)=[N:32][C:31]=2[CH:37]=1

Participants

4

Reactant 2

HCID 15550489(2S)-2-Amino-3-(4-(2-methoxycarbonyl-ethyl)-benzoylamino)-propionic acid tert-butyl esterHCID 224957925-Bromo-2-(methylthio)benzo[d]oxazole

Product 1

HCID 69733400(1,1-dimethyl ethyl) N-(5-bromo-2-benzoxazolyl)-3-[[4-(3-methoxy-3-oxo-propyl)benzoyl]amino]-L-alaninateYield 11.5%

Reagents, catalysts & solvents 1

HCID 16683746DiacetyloxymercuryCatalyst

Conditions

Temperature
75 °C

Procedure

A mixture constituted by 890 mg of 10-5, 620 mg of 5-bromo-2-methylthiobenzoxazole (prepared according to P1 but starting from 4-bromo-2-nitrophenol) and 350 mg of Hg(OAc)2 is heated for 2 hours at 75° C. then for 2 hours at 95° C. The cooled down medium is chromatographed eluting with a CH2Cl2/AcOEt mixture 82/18. 159 mg of expected product is obtained.

Workup

  1. temperatureThe cooled down medium
  2. customis chromatographed
  3. washeluting with a CH2Cl2/AcOEt mixture 82/18

Sources & evidence

ORD record
ord-e67a84d2213346f387d660aea3079512
Source dataset
uspto-grants-2005_01
Patent number
US06838453B2

Reaction notes

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