Sodium Hydroxide → HCID 66790816, compound

HRID 2041620Notes

Reaction equation

HRID 2041620 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([N:13]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:7][O:8][P:9](=[O:12])([OH:11])[OH:10].[OH-].[Na+].C(=O)(O)[O-].[Na+].O=C1CCC(=O)N1[O:42][C:43](=O)[CH:44]([NH:58][C:59]([O:61][CH3:62])=[O:60])[CH:45]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>CC(C)=O>[CH3:62][O:61][C:59](=[O:60])[NH:58][CH:44]([C:43](=[O:42])[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([N:13]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH2:14][CH:15]([CH3:16])[CH3:17])[CH2:7][O:8][P:9]([OH:10])([OH:11])=[O:12])[CH:45]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 17751171HCID 17751171, compoundHCID 57909288HCID 57909288, compound

Product 1

HCID 66790816HCID 66790816, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

57 mL (or approximately 26 mmol) of the aqueous solution of phosphoric acid mono-{6-amino-2-[(4-amino-benzenesulfonyl)-isobutyl-amino]-hexyl}ester (XIX) was neutralized with 40 mL of 1N sodium hydroxide. The pH of the solution (pH˜4-5) was then adjusted to pH=8 by adding 150 mL solution of saturated of sodium bicarbonate. To this well stirred solution was added a freshly prepared solution, in 130 mL of acetone, of methoxycarbonylamino-3,3-diphenyl-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester (13.34 g, 34 mmol) prepared according to Anderson et al J. Am. Chem. Soc. 1964, 1839. The resulting clear solution was stirred for 12 h. The reaction mixture was concentrated and the remaining aqueous phase extracted twice with ethyl acetate. The aqueous phase was then acidified with 1N hydrochloric acid and the resulting suspension extracted with ethyl acetate. The organic phase was washed with water then dried over sodium sulfate, filtered and concentrated on a rotary evaporator. The solid residue was again suspended in ethyl acetate and acidified with HCl (g). The resulting beige precipitate was collected by filtration to give 12.5 g (66%) of the title product. Purity was determined by LC_MS and is greater than 97%.

Workup

  1. additionTo this well stirred solution was added a freshly prepared solution
  2. concentrationThe reaction mixture was concentrated
  3. extractionthe remaining aqueous phase extracted twice with ethyl acetate
  4. extractionthe resulting suspension extracted with ethyl acetate
  5. washThe organic phase was washed with water
  6. dry with materialthen dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated on a rotary evaporator
  9. filtrationThe resulting beige precipitate was collected by filtration

Sources & evidence

ORD record
ord-bd3302d70d944cadb0af7654504e7548
Source dataset
uspto-grants-2013_11
Patent number
US08580995B2

Reaction notes

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