Acetic Acid → HCID 46196302, compound

HRID 1036454Notes

Reaction equation

HRID 1036454 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[CH:22]=[C:21]([C@:26]([NH:42]C(=O)OC(C)(C)C)([CH3:41])[CH2:27][O:28][P:29]([O:36]C(C)(C)C)([O:31]C(C)(C)C)=[O:30])[CH:20]=[CH:19]3)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.Cl.CCOCC>O>[P:29]([OH:31])([OH:36])([O:28][CH2:27][C@:26]([NH2:42])([C:21]1[CH:20]=[CH:19][C:18]2[C:23](=[CH:24][CH:25]=[C:16]([S:15][C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:10]=3)[CH:17]=2)[CH:22]=1)[CH3:41])=[O:30]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67530779HCID 67530779, compound

Product 1

HCID 46196302HCID 46196302, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

(R)-tert-butyl 2-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)-1-(di-tert-butoxyphosphoryloxy)propan-2-ylcarbamate was dissolved in acetic acid (2.0 mL, 0.035 mol) and 10 M hydrogen chloride in water (0.5 mL) and stirred for 1 d. Removal solvent and concentration gave an oil, which was added to water and ether. The aqueous layer was concentrated and purified by preparative HPLC 0.1% TFA water/ACN to give (R)-2-amino-2-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)propyl dihydrogen phosphate as a solid (1.1 mg, 4%). LCMS 1.56 496.25 (M+1, 40%), 991.66. HNMR shows quite pure. 1H NMR (400 MHz, MeOD) δ=7.98 (s, 1H), 7.89 (d, J=8.5 Hz, 2H), 7.82 (s, 1H), 7.65 (d, J=6.7 Hz, 1H), 7.43 (d, J=10.4 Hz, 1H), 7.39-7.25 (m, 6H), 7.05-6.95 (m, 3H), 5.06 (s, 2H), 4.29 (dd, J=5.0, 11.0 Hz, 1H), 4.16 (dd, J=5.4, 11.0 Hz, 1H), 1.86 (s, 3H).

Workup

  1. customRemoval solvent and concentration
  2. customgave an oil, which
  3. concentrationThe aqueous layer was concentrated
  4. custompurified by preparative HPLC 0.1% TFA water/ACN

Sources & evidence

ORD record
ord-e36ff12a06ac400fa78f51f544b5b380
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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