L-Glutamic acid, N-(4-aminobenzoyl)-, bis(1,1-dimethylethyl) ester → 4-[6,7-Bis(12-phenyldodecanoyloxy)-4-thiaheptanoylamino]benzoylglutamic acid di-t-butylester

HRID 1720830Notes

Reaction equation

HRID 1720830 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH:21]([CH2:29][O:30][C:31](=[O:49])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:22][S:23][CH2:24][CH2:25][C:26](O)=[O:27])=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:50]([O:54][C:55](=[O:76])[C@H:56]([CH2:67][CH2:68][C:69]([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:70])[NH:57][C:58](=[O:66])[C:59]1[CH:64]=[CH:63][C:62]([NH2:65])=[CH:61][CH:60]=1)([CH3:53])([CH3:52])[CH3:51]>N1C=CC=CC=1.P(Cl)(Cl)Cl>[C:50]([O:54][C:55](=[O:76])[C@H:56]([CH2:67][CH2:68][C:69]([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:70])[NH:57][C:58](=[O:66])[C:59]1[CH:64]=[CH:63][C:62]([NH:65][C:26](=[O:27])[CH2:25][CH2:24][S:23][CH2:22][CH:21]([O:20][C:18](=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:29][O:30][C:31](=[O:49])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)=[CH:61][CH:60]=1)([CH3:52])([CH3:53])[CH3:51]

Participants

5

Reactant 2

HCID 10691066L-Glutamic acid, N-(4-aminobenzoyl)-, bis(1,1-dimethylethyl) esterHCID 224186176,7-Bis(12-phenyldodecanoyloxy)-4-thiaheptanoic acid

Product 1

HCID 118042124-[6,7-Bis(12-phenyldodecanoyloxy)-4-thiaheptanoylamino]benzoylglutamic acid di-t-butylesterYield 93%

Reagents, catalysts & solvents 2

HCID 24387Phosphorus trichlorideCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 6,7-bis(12-phenyldodecanoyloxy)-4-thiaheptanoic acid as obtained in Reference Example 34 (200 mg) and 4-aminobenzoyl-glutamic acid di-t-butyl ester (108 mg) in pyridine (6 ml), phosphorus trichloride (4 drops) was added drop by drop, followed by stirring at room temperature for 1 hour. After the solvent was concentrated, the residue was purified by silica gel column (n-hexane:ethyl acetate=2:1) to yield the title compound (282 mg, yield 93%) as a colorless oily substance.

Workup

  1. additionwas added drop by drop
  2. concentrationAfter the solvent was concentrated
  3. customthe residue was purified by silica gel column (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-6ee756145c604cda96f8e66862a30ef3
Source dataset
uspto-grants-1996_04
Patent number
US05506267

Reaction notes

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