Methanesulfonyl chloride → HCID 86601854, compound

HRID 417810Notes

Reaction equation

HRID 417810 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:6][S:7][CH2:8][CH2:9][O:10][P:11]([N:20]([CH2:24][CH2:25][Cl:26])[CH2:21][CH2:22][Cl:23])([N:13]([CH2:17][CH2:18][Cl:19])[CH2:14][CH2:15][Cl:16])=[O:12])[NH2:5].C(N(C(C)C)CC)(C)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>O1CCCC1>[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:6][S:7][CH2:8][CH2:9][O:10][P:11]([N:13]([CH2:14][CH2:15][Cl:16])[CH2:17][CH2:18][Cl:19])([N:20]([CH2:24][CH2:25][Cl:26])[CH2:21][CH2:22][Cl:23])=[O:12])[NH:5][S:38]([CH3:37])(=[O:40])=[O:39]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531Diisopropylethylamine2×HCID 86601852HCID 86601852, compound

Product 1

HCID 86601854HCID 86601854, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[[2-[[Bis[bis(2-chloroethyl)amino]phosphinyl]oxy]ethyl]thio]-L-alanine methyl ester, 400 mg (0.8 mmol), was dissolved in 4 mL anhydrous tetrahydrofuran, and 550 μL (3.2 mmol) diisopropylethylamine added, followed by methanesulfonyl chloride, 181 mg (1.6 mmol). The reaction mixture was purged with argon and stirred overnight. After adding a further 275 μL (1.6 mmol) diisopropylethylamine, then tris(2-aminoethyl)amine-polystyrene resin, 480 mg (1.6 mmol), the mixture was agitated for 6 hours, then filtered and the filtrate evaporated to dryness under vacuum, giving N-(methanesulfonyl)-3-[[2-[[bis[bis(2-chloroethyl)amino]phosphinyl]oxy]ethyl]thio]-L-alanine methyl ester, 397 mg. Purity was verified with ELSD and identity verified with 1H and 31P NMR.

Workup

  1. customThe reaction mixture was purged with argon
  2. filtrationfiltered
  3. customthe filtrate evaporated to dryness under vacuum

Sources & evidence

ORD record
ord-34770adcdce04386897eceabe44e290b
Source dataset
uspto-grants-2012_01
Patent number
US08093231B2

Reaction notes

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