Sodium Hydroxide → HCID 10865336, compound

HRID 363403Notes

Reaction equation

HRID 363403 reaction equation
[C:1]1([CH3:47])[CH:6]=[CH:5][C:4]([S:7]([N:10]([CH2:16][CH2:17][N:18]([S:37]([C:40]2[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=2)(=[O:39])=[O:38])[CH2:19][CH2:20][N:21]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[CH2:22][C:23]([O:25]C)=[O:24])[CH2:11][C:12]([O:14]C)=[O:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH-].[Na+]>O1CCCC1>[C:33]1([CH3:36])[CH:34]=[CH:35][C:30]([S:27]([N:21]([CH2:20][CH2:19][N:18]([S:37]([C:40]2[CH:41]=[CH:42][C:43]([CH3:46])=[CH:44][CH:45]=2)(=[O:38])=[O:39])[CH2:17][CH2:16][N:10]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:47])=[CH:2][CH:3]=2)(=[O:8])=[O:9])[CH2:11][C:12]([OH:14])=[O:13])[CH2:22][C:23]([OH:25])=[O:24])(=[O:29])=[O:28])=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13764554HCID 13764554, compound

Product 1

HCID 10865336HCID 10865336, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dimethyl 3,6,9-tris(p-toluenesulfonyl)-3,6,9-triazaundecanedioate prepared as in Example 28E (16 g, 22.5 mmol) was slurried in tetrahydrofuran (100 ml). Sodium hydroxide (2N, 160 ml) was added dropwise over a 1 h period. After 72 h, the solvent was evaporated under reduced pressure, and hydrochloric acid (1N) was added to lower the pH to 4. This aqueous phase was extracted several times with ethyl acetate. The combined ethyl acetate layers were washed twice with brine, dried (MgSO4), filtered, and evaporated to give a white solid, 14.22 g (93% yield): mp 177°-80° C.; 1H NMR (DMSO-d6) δ 2.38 and 2.40 (2 s, 9 H), 3.10 (m, 4 H), 3.29 (m, 4 H), 3.73 (s, 4 H), 7.37 and 7.41 (2 d, J=7.9, 8.2 Hz, 6 H), 7.61 and 7.66 (2 d, J=8.2 , 8.0 Hz, 6 H).

Workup

  1. customthe solvent was evaporated under reduced pressure, and hydrochloric acid (1N)
  2. additionwas added
  3. extractionThis aqueous phase was extracted several times with ethyl acetate
  4. washThe combined ethyl acetate layers were washed twice with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give a white solid, 14.22 g (93% yield)

Sources & evidence

ORD record
ord-9d52fde75ca343d98aa4de1188f2c89b
Source dataset
uspto-grants-1999_02
Patent number
US05874421

Reaction notes

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