Methanesulfonyl chloride → (S)-3-(2-amino-5-(2-methoxy-4-(3-(methylsulfonyloxy)propoxy)benzyl)-6-methylpyrimidin-4-ylamino)hexyl acetate

HRID 2207094Notes

Reaction equation

HRID 2207094 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(C(C)C)CC)(C)C.[C:15]([O:18][CH2:19][CH2:20][C@@H:21]([NH:25][C:26]1[C:31]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][CH2:42][OH:43])=[CH:35][C:34]=2[O:44][CH3:45])=[C:30]([CH3:46])[N:29]=[C:28]([NH2:47])[N:27]=1)[CH2:22][CH2:23][CH3:24])(=[O:17])[CH3:16]>C1COCC1.O.C(OC([O-])=O)(O)=O.[Na+]>[C:15]([O:18][CH2:19][CH2:20][C@@H:21]([NH:25][C:26]1[C:31]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][CH2:42][O:43][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:35][C:34]=2[O:44][CH3:45])=[C:30]([CH3:46])[N:29]=[C:28]([NH2:47])[N:27]=1)[CH2:22][CH2:23][CH3:24])(=[O:17])[CH3:16]

Participants

7

Reactant 3

HCID 31297Methanesulfonyl chloride2×HCID 81531Diisopropylethylamine2×HCID 89907823(S)-3-(2-amino-5-(4-(3-hydroxypropoxy)-2-methoxybenzyl)-6-m ethylpyrimidin-4-yl-amino)hexyl acetate

Product 1

HCID 89906963(S)-3-(2-amino-5-(2-methoxy-4-(3-(methylsulfonyloxy)propoxy)benzyl)-6-methylpyrimidin-4-ylamino)hexyl acetate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 88008498Sodium hydrogen dicarbonateSolvent

Procedure

Methanesulfonyl chloride (0.083 mL) was added to a solution of diisopropylethylamine (0.279 mL) and the product from step (iv) (0.246 g) in THF (10 mL). The mixture was stirred at RT for 3 h and additional diisopropylethylamine (0.14 mL) and methanesulfonyl chloride (0.042 mL) was added. The mixture was stirred at RT for 2 h, diluted with water and sat. sodium hydrogen dicarbonate and extracted with EtOAc. The combined organic layer was dried and concentrated under reduced pressure to afford the crude product (300 mg) as a pale yellow oil, which was used for the next reaction without further purification; LC-MS: m/z 539.

Workup

  1. stirringThe mixture was stirred at RT for 2 h
  2. extractionextracted with EtOAc
  3. customThe combined organic layer was dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-11c8e35c4f0e484684d440a8945ed3d0
Source dataset
uspto-grants-2016_06
Patent number
US09376398B2

Reaction notes

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