Methanol → HCID 22672527, compound

HRID 1444789Notes

Reaction equation

HRID 1444789 reaction equation
[CH3:1][C:2]([CH3:26])([CH3:25])[C:3]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]=[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[CH:15][C:14](=[O:20])[C:13]([CH2:21][CH2:22][CH2:23][OH:24])=[CH:12]3)=[O:4].C(N(CC)CC)C.[CH:34]([N:37]([CH:45]([CH3:47])[CH3:46])[P:38](Cl)[O:39][CH2:40][CH2:41][C:42]#[N:43])([CH3:36])[CH3:35].CO>C(Cl)Cl.CCOCC.CCCCCC>[CH3:1][C:2]([CH3:26])([CH3:25])[C:3]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]=[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[CH:15][C:14](=[O:20])[C:13]([CH2:21][CH2:22][CH2:23][O:24][P:38]([N:37]([CH:45]([CH3:47])[CH3:46])[CH:34]([CH3:35])[CH3:36])[O:39][CH2:40][CH2:41][C:42]#[N:43])=[CH:12]3)=[O:4]

Participants

8

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 27348442-Cyanoethyl N,N-diisopropylchlorophosphoramiditeHCID 226725258-(3-Hydroxypropyl)-7-oxophenoxazin-3-yl 2,2-dimethylpropanoate

Product 1

HCID 22672527HCID 22672527, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

36b (0.38 g, 1.1 mmol) was dissolved in 6 mL of anhydrous CH2Cl2. Triethylamine (1.5 mL) was added followed by 2-cyanoethyl diisopropylchlorophosphoramidite (0.29 mL, 1.3 mmol). The solution was kept at room temperature for 30 min, MeOH (0.1 mL) was added and the reaction was concentrated under vacuum. The residue obtained was partitioned between ethyl acetate and NaHCO3. The organic phase was washed with saturated NaCl, dried over Na2SO4 and concentrated to afford the crude amidite. It was dissolved in 2 mL of ether and added dropwise to ˜50 mL of hexane. The resultant orange solid was collected by filtration, washed with hexane and dried. The yield was 0.4 g.

Workup

  1. concentrationthe reaction was concentrated under vacuum
  2. customThe residue obtained
  3. customwas partitioned between ethyl acetate and NaHCO3
  4. washThe organic phase was washed with saturated NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford the crude amidite
  8. filtrationThe resultant orange solid was collected by filtration
  9. washwashed with hexane
  10. customdried

Sources & evidence

ORD record
ord-1854324b44c141c4a2332bf0d2991e20
Source dataset
uspto-grants-2010_02
Patent number
US07662942B2

Reaction notes

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