HCID 11135603, compound → HCID 10188945, compound

HRID 644920Notes

Reaction equation

HRID 644920 reaction equation
[F:1][C:2]([F:36])([C:14]([F:35])([F:34])[C:15]([F:33])([F:32])[C:16]([F:31])([F:30])[C:17]([F:29])([F:28])[C:18]([F:27])([F:26])[C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])[CH2:3][CH2:4][C:5]([O:8][C:9](=[O:13])N(C)C)([CH3:7])[CH3:6].C(Cl)Cl.C(O)([C:42]([F:45])([F:44])[F:43])=O>>[F:1][C:2]([F:36])([C:14]([F:35])([F:34])[C:15]([F:33])([F:32])[C:16]([F:31])([F:30])[C:17]([F:29])([F:28])[C:18]([F:27])([F:26])[C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])[CH2:3][CH2:4][C:5]([O:8][C:9](=[O:13])[C:42]([F:45])([F:44])[F:43])([CH3:7])[CH3:6]

Participants

3

Reactant 2

HCID 11135603HCID 11135603, compoundHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 10188945HCID 10188945, compoundYield 100%

Procedure

Dimethylamine(2-perfluorooctylethyl)isopropyl carbamate 10 (251 mg, 0.44 mmol) was stirred with 1:1 CH2Cl2/TFA at room temperature overnight. After evaporation of solvent, the residue was partitioned between dichloromethane and aqueous K2CO3. The organic phase was dried over MgSO4 and evaporated to give pure product (262 mg, 100%); 1H NMR (CDCl3) δ 2.22-2.08 (m, 4H), 1.63 (s, 6H); 19F NMR (CDCl3) δ −74.6 (3F), −79.6 (2F), −113.3 (2F), −120.8 (6F), −121.6 (2F), −122.1 (2F), −125.0 (2F). 13C NMR (CDCl3) δ 156.4 (t), 121.5-105.1 (m), 86:7, 31.5, 25.7 (t), 25.0; LRMS: m/z (relative intensity) 587 (M+−Me, 70%), 489 (M+−CF3CO2, 68%), 155 (82%); HRMS calcd. for C13H10F17: 489.0511, found: 489.0504; IR (thin film): 2992, 1784, 1371, 1214 cm−1.

Workup

  1. customAfter evaporation of solvent
  2. customthe residue was partitioned between dichloromethane and aqueous K2CO3
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-7d4ece39a2ca44cd9a13a276371a9b10
Source dataset
uspto-grants-2010_04
Patent number
US07700794B2

Reaction notes

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