1,4-Dioxane → HCID 67424507, compound

HRID 2389098Notes

Reaction equation

HRID 2389098 reaction equation
C(OC(=O)[NH:7][C@@:8]([C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:30][CH:31]3[CH2:36][CH2:35][CH:34]([C:37]([CH3:41])([CH3:40])[CH2:38][CH3:39])[CH2:33][CH2:32]3)[C:22]=2[C:26]([F:29])([F:28])[F:27])[CH:17]=1)([CH3:15])[CH2:9][O:10][P:11]([OH:14])([OH:13])=[O:12])(C)(C)C.O1CCOCC1>Cl>[NH2:7][C@@:8]([C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:30][CH:31]3[CH2:32][CH2:33][CH:34]([C:37]([CH3:40])([CH3:41])[CH2:38][CH3:39])[CH2:35][CH2:36]3)[C:22]=2[C:26]([F:27])([F:28])[F:29])[CH:17]=1)([CH3:15])[CH2:9][O:10][P:11](=[O:12])([OH:13])[OH:14]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 67414439HCID 67414439, compound

Product 1

HCID 67424507HCID 67424507, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of ((R)-1-{6-[4-(1,1-dimethyl-propyl)-cyclohexyloxy]-5-trifluoromethyl-naphthalen-2-yl}-1-methyl-2-phosphonooxy-ethyl)-carbamic acid tert-butyl ester (45 mg, 0.07 mmol) in 4 M of HCl in dioxane (3 mL, 10 mmol) was stirred at room temperature for 3 hrs. After the solution was concentrated, the crude product was treated with acetonitrile to form precipitate. The precipitate was purified with a silica gel column eluted with 10% TFA in MeOH and DCM from 0 to 30% to give 24 mg of product, 63%. ESI-MS (M+H)+: 518.30, room temperature 1.70 min. 1H NMR (400 MHz, CD3OD) δ: 8.24 (d, 1H), 8.11 (d, 1H), 7.99 (s, 1H), 7.69 (s, 1H), 7.58 (s, 1H), 4.48 (m, 1H), 4.35 (m, 1H), 4.22 (m, 1H), 2.20 (d, 2H), 1.85 (s, 5H), 1.49 (m, 2H), 1.38-1.16 (m, 6H), 0.85 (m, 9H).

Workup

  1. concentrationAfter the solution was concentrated
  2. additionthe crude product was treated with acetonitrile
  3. customto form precipitate
  4. customThe precipitate was purified with a silica gel column
  5. washeluted with 10% TFA in MeOH and DCM from 0 to 30%

Sources & evidence

ORD record
ord-cc8371047d024787a5c6bcc940e92785
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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