Triethylamine → HCID 59483399, compound

HRID 1359930Notes

Reaction equation

HRID 1359930 reaction equation
[P:1]([Cl:15])(Cl)([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)=[O:2].[Cl-].[CH2:17]([O:21][C:22](=[O:26])[C@@H:23]([NH3+:25])[CH3:24])[CH2:18][CH2:19][CH3:20].CCN(CC)CC>C(Cl)Cl>[Cl:15][P:1]([NH:25][C@H:23]([C:22]([O:21][CH2:17][CH2:18][CH2:19][CH3:20])=[O:26])[CH3:24])([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5756311-DichlorophosphoryloxynaphthaleneHCID 117895531HCID 117895531, compound

Product 1

HCID 59483399HCID 59483399, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To 1-naphthyl dichlorophosphate in DCM (0.086 M) was added (25)-1-butoxy-1-oxopropan-2-aminium chloride (1.0 eq.). After cooling to −78° C., neat Et3N (2.0 eq.) was added and the reaction was left to warm to RT overnight. All volatiles were removed and the resulting white solid was washed with Et2O, filtered and evaporated in vacuo to obtain a colorless oil as a 1:1 mixture of diastereoisomers. 31P NMR (400 MHz, CDCl3): δ 8.39 and 8.11 ppm.

Workup

  1. waitthe reaction was left
  2. temperatureto warm to RT overnight
  3. customAll volatiles were removed
  4. washthe resulting white solid was washed with Et2O
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto obtain a colorless oil
  8. additionas a 1:1 mixture of diastereoisomers

Sources & evidence

ORD record
ord-5ed23c939c864e90ad752df79c214073
Source dataset
uspto-grants-2011_02
Patent number
US07879815B2

Reaction notes

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