N-Methylpropylamine → HCID 10603036, compound

HRID 1603992Notes

Reaction equation

HRID 1603992 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]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:18]=[C:17]([C:33]([O:35][CH:36]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:34])[O:16]1)=O.[CH3:49][NH:50][CH2:51][CH2:52][CH3:53]>>[CH:36]([O:35][C:33]([C:17]1[O:16][C@@H:15]([C:13](=[O:12])[N:50]([CH3:49])[CH2:51][CH2:52][CH3:53])[C@H:20]([NH:21][C:22](=[O:24])[CH3:23])[C@@H:19]([NH:25][C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH:18]=1)=[O:34])([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

3

Reactant 2

HCID 12315N-MethylpropylamineHCID 10676004HCID 10676004, compound

Product 1

HCID 10603036HCID 10603036, compound

Conditions

Temperature
23 °C

Procedure

To (2R,3R,4S)-3-acetylamino-4-(tert-butoxycarbonylamino)-3,4-dihydro-2H-pyran-2,6-dicarboxylic acid 6-benzhydryl ester 2-(2,3,4,5,6-pentafluoro-phenyl) ester (1.18 g) in dry tetrahydroduran (13 ml) was added N-methyl-propylamine (0.152 g) and the reaction was stirred at 23° C. for 4 hours. The solvent was removed in vacuo and the residue was chromatographed over silica (Merck 9385, 150 g) using medium pressure (~4 psi) and ethyl acetate as the eluant. The required fractions were combined and the solvent removed in vacuo to give the title compound as a white foam. (0.85 g); 1H NMR (250 MHz, D6 -DMSO) 8.10-7.98 (1H, m), 7.48-7.26 (10H, m), 6.91 (1H, s), 6.58 (1H, m), 6.03 (1H, m), 5.13 (1H, m), 4.34 (1H, m), 4.03 (1H, m), 3.37 (2H, m), 3.07+2.81 (3H, s), 1.77 (3H, s), 1.64-1.22 (2H, m), 1.37 (9H, s), 0.81 (3H, m): Mass spec (Low resolution): MH+ =566, MH+ -BOC=466; Mass analysis:

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was chromatographed over silica (Merck 9385, 150 g)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d0d2a3cab8c14bf58b1d7c9d8603a130
Source dataset
uspto-grants-1999_11
Patent number
US05990156

Reaction notes

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