Triethylamine → HCID 67952054, compound

HRID 404266Notes

Reaction equation

HRID 404266 reaction equation
S(C1C=CC(C)=CC=1)(O)(=O)=O.[NH2:12][C@@H:13]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25](=[O:38])[C:26]([CH3:37])([O:28][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH3:27])=[C:20]([O:39][C:40](=[O:53])[C:41]([O:44][C:45](=[O:52])[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)([CH3:43])[CH3:42])[CH:19]=1)[C:14]([OH:16])=[O:15].C(N(CC)CC)C>C(#N)C.O>[NH2:12][C@@H:13]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25](=[O:38])[C:26]([CH3:27])([O:28][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH3:37])=[C:20]([O:39][C:40](=[O:53])[C:41]([O:44][C:45](=[O:52])[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)([CH3:43])[CH3:42])[CH:19]=1)[C:14]([OH:16])=[O:15]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86696601HCID 86696601, compound2×

Product 1

HCID 67952054HCID 67952054, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of the type A crystal of (2S)-2-amino-3-(3,4-bis((2-(benzoyloxy)-2-methylpropanoyl)oxy)phenyl)propanoic acid tosylate produced in Example 6 or the type B crystal of (2S)-2-amino-3-(3,4-bis((2-(benzoyloxy)-2-methylpropanoyl)oxy)phenyl)propanoic acid tosylate produced in Example 7 (167 g) in acetonitrile (2080 mL) and water (42 mL), a solution of triethylamine (21.4 g) in acetonitrile (420 mL) was added dropwise. After the reaction mixture was stirred for 16 hours, a deposited solid was obtained by filtration and washed with acetonitrile (500 mL). Then, the solid was dried at 50° C. for 16 hours, whereby a crude product of the title compound (106 g, 81%) was obtained as a white solid.

Workup

  1. customa deposited solid was obtained by filtration
  2. washwashed with acetonitrile (500 mL)
  3. customThen, the solid was dried at 50° C. for 16 hours

Sources & evidence

ORD record
ord-bf4a6fde027f4c208929779460e0ef30
Source dataset
uspto-grants-2014_06
Patent number
US08748485B2

Reaction notes

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