Triethylamine → benzyl (2S,3S)-3-hydroxy-2-(2-(6-(trifluoromethyl)quinazolin-4-ylamino)acetamido)hex-4-ynylcarbamate

HRID 2250809Notes

Reaction equation

HRID 2250809 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C@@H:19]([OH:23])[C:20]#[C:21][CH3:22])[CH2:7][NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4].C(N(CC)CC)C.Cl[C:32]1[C:41]2[C:36](=[CH:37][CH:38]=[C:39]([C:42]([F:45])([F:44])[F:43])[CH:40]=2)[N:35]=[CH:34][N:33]=1>CCO>[OH:23][C@@H:19]([C:20]#[C:21][CH3:22])[C@@H:6]([NH:5][C:3](=[O:4])[CH2:2][NH:1][C:32]1[C:41]2[C:36](=[CH:37][CH:38]=[C:39]([C:42]([F:44])([F:45])[F:43])[CH:40]=2)[N:35]=[CH:34][N:33]=1)[CH2:7][NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 210750954-Chloro-6-(trifluoromethyl)quinazolineHCID 86596714benzyl (2S,3S)-2-(2-aminoacetamido)-3-hydroxyhex-4-ynylcarbamate

Product 1

HCID 86596718benzyl (2S,3S)-3-hydroxy-2-(2-(6-(trifluoromethyl)quinazolin-4-ylamino)acetamido)hex-4-ynylcarbamateYield 59.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzyl (2S,3S)-2-(2-aminoacetamido)-3-hydroxyhex-4-ynylcarbamate (194 mg, see procedure 15a) was dissolved in EtOH (3 mL) and the resultant solution was charged with triethylamine (0.42 mL) and 4-chloro-6-(trifluoromethyl)quinazoline (141 mg). The mixture was heated at 80 C for 14 h, cooled to RT, and concentrated in vacuo to afford benzyl (2S,3S)-3-hydroxy-2-(2-(6-(trifluoromethyl)quinazolin-4-ylamino)acetamido)hex-4-ynylcarbamate (186 mg). MS found: (M+H)+=516.3.

Workup

  1. temperatureThe mixture was heated at 80 C for 14 h
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03b0aff07fe94c69872b22b0fdee17c2
Source dataset
uspto-grants-2008_01
Patent number
US07317019B2

Reaction notes

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