Methanol → HCID 136341186, compound

HRID 2249155Notes

Reaction equation

HRID 2249155 reaction equation
C(OC([NH:11][C@H:12]([C:17]([O:19][CH2:20][CH:21]([O:42][CH2:43][N:44]1[CH:52]=[N:51][C:50]2[C:49](=[O:53])[NH:48][C:47]([NH2:54])=[N:46][C:45]1=2)[CH2:22][O:23][C:24](=[O:41])[C@H:25]([C@H:37]([CH2:39][CH3:40])[CH3:38])[NH:26]C(OCC1C=CC=CC=1)=O)=[O:18])[C@H:13]([CH2:15][CH3:16])[CH3:14])=O)C1C=CC=CC=1.C(Cl)Cl.CO.C(O)(C(F)(F)F)=O>[Pd].C(O)(=O)C.O>[NH2:26][C@H:25]([C:24]([O:23][CH2:22][CH:21]([O:42][CH2:43][N:44]1[CH:52]=[N:51][C:50]2[C:49](=[O:53])[NH:48][C:47]([NH2:54])=[N:46][C:45]1=2)[CH2:20][O:19][C:17](=[O:18])[C@H:12]([C@H:13]([CH2:15][CH3:16])[CH3:14])[NH2:11])=[O:41])[C@H:37]([CH2:39][CH3:40])[CH3:38]

Participants

8

Reactant 4

HCID 887Methanol2×HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 136341187HCID 136341187, compound

Product 1

HCID 136341186HCID 136341186, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of the product of stage (a) (2.0 g, 2.66 mmol) and 10% palladium on carbon (250 mg, Aldrich) in glacial acetic acid (250 ml) was shaken on a Parr Hydrogenator under 30 to 35 psi H2 for 5 hours. Reaction progress was monitored by TLC (silica gel, CH2Cl2 :MeOH/9:1). The catalyst was removed by filtration (Millipore Prefilter). Dilution of the filtrate with ether caused the product to separate as an oil. After 14 hours at 5° C., the supernatant was decanted from a colourless gum, which was dried under high vacuum to a white foam. The foam was dissolved in water (20 ml), filtered, and freeze-dried to a white foam; yield, 1.3 g (79%). H-NMR (DMSO-d6) 7.79(3,1H), 6.49(br s,2H), 5.41(s,2H), 3.9-4.2(m,4H), 3.10(d,1H), 3.06(d,1H), 1.9 (HOAc), 1.5(m,1H), 1.34(m,4H), 1.1(m,4H); 0.73-0.78(m,12H), 13C-NMR (DMSO-d6) 156.80, 153.96, 151.30, 137.47, 116.30, 73.41, 70.78, 62.88, 62.57, 58.15, 24.18, 21.28, 15.33, 15.28, 11.33; HPLC (Versapack C-18; 30% MeOH (aq.)/0.1% TFA) 1 peak, k'=1.22; UV max (H2O) 251 nm (12,000). MS (positive ion/Cl) m/z 482. Anal. Calcd. for C21H 35 N7O6.2HOAc:1H2O: C,48.46; H,7.32; N,15.82. Found: C,48.52; H,7.3; N,15.75.

Workup

  1. customReaction progress
  2. customThe catalyst was removed by filtration (Millipore Prefilter)
  3. customto separate as an oil
  4. customthe supernatant was decanted from a colourless gum, which
  5. customwas dried under high vacuum to a white foam
  6. dissolutionThe foam was dissolved in water (20 ml)
  7. filtrationfiltered
  8. customfreeze-dried to a white foam
  9. customyield

Sources & evidence

ORD record
ord-9818dbe39d2d4325b64a8cbc356c65f9
Source dataset
uspto-grants-1991_08
Patent number
US05043339

Reaction notes

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