Dipropylamine → HCID 178457287, compound

HRID 1603996Notes

Reaction equation

HRID 1603996 reaction equation
FC1C(F)=C(F)C(F)=C(F)C=1[O:12][C:13]([C@H:15]1[C@H:20]([NH:21][C:22](=[O:24])[CH3:23])[C@@H:19]([NH:25][C:26]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[N:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:18]=[C:17]([C:43]([O:45][CH:46]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[O:44])[O:16]1)=O.[CH2:59]([NH:62][CH2:63][CH2:64][CH3:65])[CH2:60][CH3:61]>O1CCCC1>[CH:46]([O:45][C:43]([C:17]1[O:16][C@@H:15]([C:13](=[O:12])[N:62]([CH2:63][CH2:64][CH3:65])[CH2:59][CH2:60][CH3:61])[C@H:20]([NH:21][C:22](=[O:24])[CH3:23])[C@@H:19]([NH:25][C:26]([NH:35][C:36]([O:38][C:39]([CH3:41])([CH3:42])[CH3:40])=[O:37])=[N:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:18]=1)=[O:44])([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 178475055HCID 178475055, compound

Product 1

HCID 178457287HCID 178457287, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (2R,3R,4S)-3-Acetylamino-4-[2,3-bis(tert-butoxycarbonyl)-guanidino]-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-benzhydryl ester 2-(2,3,4,5,6-pentafluoro-phenyl) ester (0.70 g) in dry tetrahydrofuran (5 ml) was added dipropylamine (0.141 g) and the reaction was stirred at 23° C. for 4 hours. The solvent was removed in vacuo and the residue was chromatographed on silica gel (Merck 9385, 50 g) using medium pressure (~4psi) and cyclohexane/ethyl acetate (1:1 v/v) as the eluant. The required fractions were combined and the solvent removed in vacuo to give the title compound as a pale yellow foam. (0.341 g). 1H NMR (250MHz, D6 -DMSO) 11.46 (1H, s), 8.27 (1H, d, J=6.25 Hz), 8.16 (1H, d, J=7.5Hz), 7.48--7.27 (10H, m), 6.97 (1H, s), 6.14 (1H, d, J=5Hz), 5.18 (1H, m), 4.67 (1H, m), 4.10 (1H, m), 3.61--3.24 (3H, m), 3.14 (1H, m), 1.84 (3H, s), 1.60--1.34 (4H, m), 1.46 (9H, s), 1.40 (9H, s), 0.85 (3H, t, J=7Hz), 0.74 (3H, t, J=7Hz); Mass Analysis; C39H53N5O9. 1.0C6HF5O. Required: C, 58.75; H, 5.92; N, 7.61. Found C, 58.64; H, 5.75; N, 7.61.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was chromatographed on silica gel (Merck 9385, 50 g)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-6016910ba106405fa7818ecbc19f43f8
Source dataset
uspto-grants-1999_11
Patent number
US05990156

Reaction notes

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