Aminoisobutyric acid → N-[4-(hexadecylamino)benzoyl]-2-methylalanine

HRID 1980194

Reaction equation

HRID 1980194 reaction equation
[NH2:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4].C(N(CC)CC)C.FC(F)(F)C([N:19]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[C:20]1[CH:35]=[CH:34][C:23]([C:24](ON2C(=O)CCC2=O)=[O:25])=[CH:22][CH:21]=1)=O.[OH-].[Na+]>O.C(O)C>[CH2:36]([NH:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([NH:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4])=[O:25])=[CH:34][CH:35]=1)[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51]

Participants

7

Reactant 4

HCID 6119Aminoisobutyric acidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 20437360N-[N-trifluoroacetyl-4-(hexadecylamino)benzoyloxy]succinimide

Product 1

HCID 20437359N-[4-(hexadecylamino)benzoyl]-2-methylalanine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of 103 mg. of 2-aminoisobutyric acid and 4.5 ml. of triethylamine in 1.5 ml. of water is added a solution of 550 mg. of N-[N-trifluoroacetyl-4-(hexadecylamino)benzoyloxy]succinimide in 4.5 ml. of ethanol. The mixture is stirred for 23 hours at room temperature, treated with 2 ml. of 2N sodium hydroxide solution, and then acidified. The mixture is diluted with water and then filtered. Recrystallization from ether-hexane affords the title compound as a white solid.

Workup

  1. additiontreated with 2 ml
  2. filtrationfiltered
  3. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-98a5fc3e98d04151ae869e37df036a9a
Source dataset
uspto-grants-1984_11
Patent number
US04485105

Linked notes

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