Triethylamine → HCID 86675997, compound

HRID 475437Notes

Reaction equation

HRID 475437 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[C:27]2[CH:28]=[CH:29][C:30]([C:32]([OH:34])=O)=[CH:31][C:26]=2[O:25][N:24]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.S(Cl)([Cl:44])=O>ClCCl>[Cl:44][C:32]([C:30]1[CH:29]=[CH:28][C:27]2[C:23]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)=[N:24][O:25][C:26]=2[CH:31]=1)=[O:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 70802833HCID 70802833, compound2×

Product 1

HCID 86675997HCID 86675997, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-(1(S)-(tert-butoxycarbonylamino)-2-(pyridin-2-yl)ethyl) -phenyl)benzo[d]isoxazole-6-carboxylic acid (Compound 18a) (45 mg) dissolved in dry dichloromethane (2 mL) under nitrogen, cooled with ice bath, was added triethylamine (127 μL) then thionyl chloride (35.5 μL). After 10 min the solvents were removed under reduced pressure to give the title product.

Workup

  1. temperaturecooled with ice bath
  2. customAfter 10 min the solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-1c3e36b0ae5f4064b02ce7b703040aaa
Source dataset
uspto-grants-2014_01
Patent number
US08637551B2

Reaction notes

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