HCID 18605744, compound → HCID 18605745, compound

HRID 1249220Notes

Reaction equation

HRID 1249220 reaction equation
C([O:8][C:9](=[O:58])[C@H:10]([CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[NH:11][C:12](=[O:50])[CH2:13][CH:14]([O:30][C:31](=[O:49])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38](=[O:48])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][NH:44][C:45](=[O:47])[CH3:46])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])C1C=CC=CC=1>O1CCCC1.CO.[Pd]>[C:45]([NH:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][C:38]([NH:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][C:31]([O:30][CH:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:13][C:12]([NH:11][C@H:10]([C:9]([OH:58])=[O:8])[CH2:51][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)=[O:50])=[O:49])=[O:48])(=[O:47])[CH3:46]

Participants

5

Reactant 1

HCID 18605744HCID 18605744, compound

Product 1

HCID 18605745HCID 18605745, compoundYield 76.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.80 g of the above ester compound was treated with 8 ml of TFA to convert the ester to free carboxylic acid and after adding thereto 5 ml of methylenechloride, 1.20 g of L-phenylalanine benzyl ester TsOH salt, 0.4 ml of TEA and 590 mg of DCC, the mixture was trated in the same manner as in Example 14-(ii) to provide 740 mg of N-[3-[6-(6-acetamidohexanamido)hexanoyloxy]octadecanoyl]-L-phenylalanine benzyl ester. 660 mg of the ester compound thus were dissolved in a mixture of 30 ml of tetrahydrofuran and 15 ml of methanol and after carrying out catalytic reduction by using 100 mg of 10% Pd-C and treating in the same manner as in Example 23-(iv), 450 mg of N-[3-[6-(6-acetamidohexanamido)hexanoyloxy]octadecanoyl]-L-phenylalanine was obtained.

Workup

  1. additiontreating in the same manner as in Example 23-(iv)

Sources & evidence

ORD record
ord-a9614d507e874a439c7f614e10b4ed99
Source dataset
uspto-grants-1986_12
Patent number
US04629736

Reaction notes

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