Triethylamine → HCID 57057672, compound

HRID 1684748Notes

Reaction equation

HRID 1684748 reaction equation
C(N(CC)CC)C.[N+](C1C=C[C:14]([O:17]C=O)=CC=1)([O-])=O.Cl.[NH2:21][C@H:22]([C@@H:46]([OH:57])[CH2:47][C@H:48]([C:50](=[O:56])[NH:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH3:49])[CH2:23][C@@H:24]([CH:43]([CH3:45])[CH3:44])[CH2:25][NH:26][C:27](=[O:42])[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[C:29]=1[O:36][CH2:37][CH2:38][CH2:39][O:40][CH3:41]>ClCCl>[CH2:52]([NH:51][C:50]([C@H:48]([CH3:49])[CH2:47][C@H:46]([OH:57])[C@@H:22]([NH:21][CH:14]=[O:17])[CH2:23][C@@H:24]([CH:43]([CH3:45])[CH3:44])[CH2:25][NH:26][C:27](=[O:42])[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[C:29]=1[O:36][CH2:37][CH2:38][CH2:39][O:40][CH3:41])=[O:56])[CH2:53][CH2:54][CH3:55]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 746284-Nitrophenyl formateHCID 69646341HCID 69646341, compound

Product 1

HCID 57057672HCID 57057672, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.034 ml) and formic acid 4-nitrophenyl ester (28 mg) are added at room temperature, with stirring, to a solution of (2S,4S,5S,7R)-N-(4-amino-7-butylcarbamoyl-5-hydroxy-2-isopropyl-octyl)-3-methoxy-2-(3-methoxypropoxy)-benzamide hydrochloride (Example 6a) (67 mg) in dichloromethane (4 ml). The resulting reaction solution is stirred for a further 30 minutes and is then concentrated by evaporation. The residue is purified by FC (18 g of silica gel; eluant E, then ethyl acetate-hexane-methanol 5:5:1). (2S,4S,5S,7R)-N-(7-Butylcarbamoyl-4-formylamino-5-hydroxy-2-isopropyl-octyl)-3-methoxy-2-(3-methoxypropoxy)-benzamide is obtained in the form of a white foam: Rf (L)=0.58. HPLC Rt =13.2 min. MS(FAB) m/e 552 (M+ +1).

Workup

  1. customThe resulting reaction solution
  2. concentrationis then concentrated by evaporation
  3. customThe residue is purified by FC (18 g of silica gel

Sources & evidence

ORD record
ord-d6283aeea7d740438e689a544db18584
Source dataset
uspto-grants-1997_06
Patent number
US05641778

Reaction notes

Loading…