Hydrochloric Acid → HCID 86605356, compound

HRID 132524Notes

Reaction equation

HRID 132524 reaction equation
[CH:1]([O:4][P:5]([CH2:11][O:12][CH2:13][N:14]1[C:22]([CH2:23][CH2:24][CH2:25][O:26]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2(OC)C=CC=CC2)=[N:21][C:20]2[C:15]1=[N:16][C:17]([C:51]([C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[N:18][C:19]=2[NH:48][O:49][CH3:50])([O:7][CH:8]([CH3:10])[CH3:9])=[O:6])([CH3:3])[CH3:2].Cl.[OH-].[Na+]>C(#N)C.O>[CH:8]([O:7][P:5]([CH2:11][O:12][CH2:13][N:14]1[C:22]([CH2:23][CH2:24][CH2:25][OH:26])=[N:21][C:20]2[C:15]1=[N:16][C:17]([C:51]([C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)([C:64]1[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1)[C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1)=[N:18][C:19]=2[NH:48][O:49][CH3:50])([O:4][CH:1]([CH3:3])[CH3:2])=[O:6])([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86605357HCID 86605357, compound

Product 1

HCID 86605356HCID 86605356, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 35 (52.2 g, 55.18 mmol) in acetonitrile (2 L) is treated with conc. HCl (4 mL) at room temperature and the mixture is stirred for 24 h. The reaction is neutralized with 2N NaOH and diluted with water (250 mL). It is then concentrated to remove most of acetonitrile and treated with ethyl acetate (500 mL) and water (200 mL). The organic layer is separated and dried over MgSO4. After filtration, the filtrate is concentrated and the residue is purified on a silica gel column using ethyl acetate:hexanes:methanol (1:1:0 to 1:1:0.2) as eluent to give 6.18 g (17%) of 36 as a white solid: 1H NMR (DMSO-d6): δ 8.27 (s, 1H), 7.93 (s, 1H), 7.38-7.20 (m, 13H), 6.89 (d, J=9.0 Hz, 2H), 4.92-4.80 (m, 1H), 4.64 (t, J=5.1 Hz, 1H), 4.50-4.36 (m, 2H), 4.14 (t, J=9.8 Hz, 1H), 3.89-3.65 (m, 3H), 3.76 (s, 3H), 3.42-3.18 (m, 2H), 2.22-1.95 (m, 2H), 1.18-1.11 (m, 6H), 1.06 (d, J=6.2 Hz, 6H). IR (KBr, cm−1) 3418, 2978, 1605, 1503 and 1250. Anal. Calcd for C36H44N5O6P.0.5 H2O: C, 63.33; H, 6.64; N, 10.26. Found: C, 63.31; H, 6.47; N, 10.19.

Workup

  1. concentrationIt is then concentrated
  2. customto remove most of acetonitrile
  3. additiontreated with ethyl acetate (500 mL) and water (200 mL)
  4. customThe organic layer is separated
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. concentrationthe filtrate is concentrated
  8. customthe residue is purified on a silica gel column

Sources & evidence

ORD record
ord-546a7ae0316545b681c0725191c21b24
Source dataset
uspto-grants-2008_06
Patent number
US07388002B2

Reaction notes

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