Triethylamine → (3-{[Methanesulfonyl-(4-thiazol-2-yl-benzyl)-amino]-methyl}-phenoxy)-acetic Acid Tert-butyl Ester

HRID 1699046Notes

Reaction equation

HRID 1699046 reaction equation
[C:1]([O:5][C:6](=[O:29])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[S:25][CH:26]=[CH:27][N:28]=3)=[CH:20][CH:19]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:29])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([S:38]([CH3:37])(=[O:40])=[O:39])[CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[S:25][CH:26]=[CH:27][N:28]=3)=[CH:22][CH:23]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53752425{3-[(4-Thiazol-2-yl-benzylamino)-methyl]-phenoxy}-acetic Acid Tert-butyl Ester

Product 1

HCID 57278594(3-{[Methanesulfonyl-(4-thiazol-2-yl-benzyl)-amino]-methyl}-phenoxy)-acetic Acid Tert-butyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ({3-[(4-thiazol-2-yl-benzylamino)-methyl]-phenoxy}-acetic acid tert-butyl ester (0.045 g, 0.109 mmol), triethylamine (16.8 mL, 0.120 mmol) and methanesulfonyl chloride (8.6 ml, 0.11 mmol) in 2 mL CH2Cl2 was stirred at room temperature for 2 hours. The reaction was quenched with water. The aqueous solution was washed with CH2Cl2 and the organic solution was dried over Na2SO4, filtered, and concentrated. The product was purified via flash chromatography on silica gel (1/1 EtOAc/Hexanes) to afford the title compound of Step B as a clear oil. 1H NMR (400 MHz, CDCl3) δ7.97 (d, 2H), 7.85 (s, 1H), 7.35 (m, 3H), 7.32 (m, 1H), 6.80-6.90 (m, 3H), 4.48 (s, 2H), 4.36 (s, 2H), 4.29 (s, 2H), 2.79 (s, 3H), 1.47 (s, 9H), MS 489 (M+1).

Workup

  1. customThe reaction was quenched with water
  2. washThe aqueous solution was washed with CH2Cl2
  3. dry with materialthe organic solution was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified via flash chromatography on silica gel (1/1 EtOAc/Hexanes)

Sources & evidence

ORD record
ord-36f75a1b4c16440397d17368a1584c5f
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

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