Acetic Anhydride → HCID 53984955, compound

HRID 744822Notes

Reaction equation

HRID 744822 reaction equation
C(N(CC)CC)C.[C:8]([O:11][C:12](=[O:14])[CH3:13])(=O)[CH3:9].OCC[CH2:18][CH2:19][NH:20][C:21](=[O:56])[C@H:22]([CH3:55])[CH2:23][C@H:24]([OH:54])[C@@H:25]([NH:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:26][C@@H:27]([CH:43]([CH3:45])[CH3:44])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH2:38][CH2:39][CH2:40][O:41][CH3:42])[CH:30]=1>CN(C1C=CN=CC=1)C.O1CCCC1>[C:12]([O:11][CH2:8][CH2:9][CH2:18][CH2:19][NH:20][C:21](=[O:56])[C@H:22]([CH3:55])[CH2:23][C@H:24]([OH:54])[C@@H:25]([NH:46][C:47]([O:49][C:50]([CH3:51])([CH3:53])[CH3:52])=[O:48])[CH2:26][C@@H:27]([CH:43]([CH3:45])[CH3:44])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH2:38][CH2:39][CH2:40][O:41][CH3:42])[CH:30]=1)(=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 54099801HCID 54099801, compound

Product 1

HCID 53984955HCID 53984955, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

30 ml of triethylamine, 2 mg of 4-(N,N'-dimethylamino)pyridine (DMAP) and 20 ml of acetic anhydride are added at 0° C. to 116 mg of 5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7(S)-isopropyl-2(R)-methyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid [N-(4-hydroxybutyl)]amide (Example 93) in 5 ml of tetrahydrofuran. The reaction solution is stirred for 18 hours at room temperature. The reaction mixture is partitioned between diethyl ether and water/saturated sodium chloride solution. The organic phases are concentrated by evaporation and the residue is purified by FC (40 g of silica gel, eluant: dichloromethane/methanol=95:5). The title compound is obtained: Rf (dichloromethane/methanol=9:1)=0.60.

Workup

  1. customThe reaction mixture is partitioned between diethyl ether and water/saturated sodium chloride solution
  2. concentrationThe organic phases are concentrated by evaporation
  3. customthe residue is purified by FC (40 g of silica gel, eluant: dichloromethane/methanol=95:5)

Sources & evidence

ORD record
ord-301af63c94cd48e39c8d56e61183e92d
Source dataset
uspto-grants-1996_09
Patent number
US05559111

Reaction notes

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