HCID 22242594, compound → HCID 22242603, compound

HRID 890915Notes

Reaction equation

HRID 890915 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[SH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][NH3+:38].N1C=CC=CC=1S[S:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][O:58][CH2:59][CH2:60][O:61][CH2:62][CH2:63][O:64][CH2:65][CH2:66][OH:67]>CO>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[OH:67][CH2:66][CH2:65][O:64][CH2:63][CH2:62][O:61][CH2:60][CH2:59][O:58][CH2:57][CH2:56][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][S:46][S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][NH3+:38]

Participants

4

Reactant 2

HCID 22242594HCID 22242594, compoundHCID 22242600HCID 22242600, compound

Product 1

HCID 22242603HCID 22242603, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7 (120 mg, 0.2 mmol) in 5 mL of MeOH was added 9 (101 mg, 0.22 mmol). The solution was stirred at room temperature for 33 hours. After concentration, the reaction mixture was purified by flash chromatography (gradient: CH2Cl2/MeOH, 20:1 to 10:1 to 5:1, v/v) to afford 137 mg of impure 8. 1H NMR 400 MHz (CD3OD) d 3.85 (t, J=4.8 Hz, 2H), 3.76–3.52 (m, 32H), 3.42 (m, 4H), 3.14 (t, J=4.8 Hz, 2H), 2.65 (t, J=7.4 Hz, 4H), 1.67 (m, 2H), 1.55 (m, 2H), 1.40–1.18 (br m, 32H).

Workup

  1. concentrationAfter concentration
  2. customthe reaction mixture was purified by flash chromatography (gradient
  3. customCH2Cl2/MeOH, 20:1 to 10:1 to 5:1, v/v) to afford 137 mg of impure 8

Sources & evidence

ORD record
ord-f1b95f24034f4ef7ae3241c5dc4609cf
Source dataset
uspto-grants-2006_02
Patent number
US07001740B2

Reaction notes

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