Phosphate → HCID 86590602, compound

HRID 1824444Notes

Reaction equation

HRID 1824444 reaction equation
C([SiH2][O:6][C:7](C)(C)[CH:8]([NH:17][C:18]([CH:20]1[N:24]2[C:25](=[O:44])[CH:26]([NH:31][C:32]([C:34]3[CH:43]=[CH:42][C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH:35]=3)=[O:33])[CH2:27][CH:28]=[CH:29][CH2:30][CH:23]2[CH2:22][CH2:21]1)=[O:19])[CH2:9][C:10]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[O:11])(C)(C)C.P([O-])([O-])([O-])=O>C1COCC1.N1C=CC=CC=1>[OH:6][CH2:7][CH:8]([NH:17][C:18]([CH:20]1[N:24]2[C:25](=[O:44])[CH:26]([NH:31][C:32]([C:34]3[CH:43]=[CH:42][C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH:35]=3)=[O:33])[CH2:27][CH:28]=[CH:29][CH2:30][CH:23]2[CH2:22][CH2:21]1)=[O:19])[CH2:9][C:10]([NH:12][S:13]([CH3:16])(=[O:14])=[O:15])=[O:11]

Participants

5

Reactant 2

HCID 1061PhosphateHCID 131725734HCID 131725734, compound

Product 1

HCID 86590602HCID 86590602, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-[(Naphthalene-2-carbonyl)-amino]-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid [1-(tert-butyl-dimethyl-silanyloxymethyl)-3-methanesulfonylamino-3-oxo-propyl]-amide (160 mg, 0.24 mmol) in THF (6 mL) at 0 C. is added HF in pyridine (0.3 mL). The solution is stirred at 0 C. for 1 h, poured into pH=7 phosphate buffer, and extracted with CH2Cl2. The combined organic extracts are washed with brine, dried (Na2SO4), filtered, and concentrated. The crude residue obtained is purified by flash chromatography on silica gel (CH2Cl2/MeOH) to yield 86 mg of desired product. 1H NMR (CDCl3) δ 8.34 (s, 1H), 7.91–7.79 (m, 4H), 7.49 (m, 2H), 7.09 (d, J=8.4 Hz, 1H), 5.88 (m, 2H, 5.45 (m, 1H), 4.43 (m, 1H), 4.20 (m, 2H), 3.04 (s, 3H), 3.80–1.80 (series of m, 12H).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue obtained
  7. customis purified by flash chromatography on silica gel (CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-e671552758244177a7e1e3d830200fd1
Source dataset
uspto-grants-2006_05
Patent number
US07041696B2

Reaction notes

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