Triethylamine → HCID 86665997, compound

HRID 1522326Notes

Reaction equation

HRID 1522326 reaction equation
[CH2:1]([O:3][P:4]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28](C1NC=CN=1)=[O:29])([O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)=[O:5])[CH3:2].[Cl-].[N:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[S:42][S:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][O:55][CH2:56][CH2:57][O:58][CH2:59][CH2:60][O:61][CH2:62][CH2:63][NH3+:64].CCN(CC)CC>CN(C=O)C>[N+:13]([C:10]1[CH:9]=[CH:8][C:7]([O:6][P:4]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28](=[O:29])[NH:64][CH2:63][CH2:62][O:61][CH2:60][CH2:59][O:58][CH2:57][CH2:56][O:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][S:43][S:42][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][N:36]=2)(=[O:5])[O:3][CH2:1][CH3:2])=[CH:12][CH:11]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21080071HCID 21080071, compoundHCID 86665995HCID 86665995, compound

Product 1

HCID 86665997HCID 86665997, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of phosphonate 17 (68 mg, 0.14 mmol), amino disulfide 18 (60 mg, 0.13 mmol), and Et3N (35 mL, 0.25 mmol) dissolved in DMF was stirred at 60° C. for 66 h. After concentration of the reaction mixture, the crude residue was purified by column chromatography (hexane/EA=1:1) to afford the disulfide, which contained approximately 20% starting materials. ′H NMR (CDCl3, 500 MHz) δ 8.44 (s, 1H), 8.32 (s, 1H), 8.21 (d, J=9 Hz, 2H), 7.78 (br s, 1H), 7.70 (br s, 1H), 7.32 (d, J=9.0 Hz, 2H), 7.07 (br s, 1H), 4.15 (m, 2H), 3.98 (m, 2H), 3.62-3.49 (br m, 10H), 3.45 (m, 2H), 3.32 (m, 2H), 2.78 (t, J=7.5 Hz, 2H), 1.90 (m, 2H), 1.79 (m, 2H), 1.71-1.44 (br m, 4H), 1.40-1.07 (br, 33H).

Workup

  1. customAfter concentration of the reaction mixture, the crude residue was purified by column chromatography (hexane/EA=1:1)

Sources & evidence

ORD record
ord-c6b373653bd34bd1a92aa775ac9584c5
Source dataset
uspto-grants-2015_07
Patent number
US09074300B2

Reaction notes

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