Triethylamine → HCID 86585984, compound

HRID 1935634Notes

Reaction equation

HRID 1935634 reaction equation
[CH3:1][C:2]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N:14]3[CH2:18][C@H:17]([CH2:19][OH:20])[O:16][C:15]3=[O:21])[CH:11]=2)[N:6]1[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])([CH3:4])[CH3:3].C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C(Cl)Cl>[CH3:4][C:2]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N:14]3[CH2:18][C@H:17]([CH2:19][O:20][S:40]([CH3:39])(=[O:42])=[O:41])[O:16][C:15]3=[O:21])[CH:11]=2)[N:6]1[C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69946365HCID 69946365, compound

Product 1

HCID 86585984HCID 86585984, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The alcohol prepared in Step 5 (11.3 g, 26.6 mmol) is dissolved in CH2Cl2 (125 ml) with triethylamine (11.0 ml, 79 mmol) and cooled to 0°. Methanesulfonylchloride (2.4 ml, 31 mmol) is added and the reaction stirred for 2 hours. Extra CH2Cl2 (100 ml) is added and the solution washed with water (100 ml) and brine (50 ml) then dried (MgSO4). Evaporation gave a gum which is chromatographed over silica gel (500 g) eluting with 25-60% ethyl acetate-hexane. The product is obtained as a white foam (10.95 g, 82%): HRMS (FAB): Calcd for m+Na=525.1672; Found: 525.1671. Anal: Calcd. for C25H30N2O7S: C, 59.74; H, 6.02; N, 5.57. Found: C, 59.44; H, 6.07; N, 5.49.

Workup

  1. temperaturecooled to 0°
  2. washthe solution washed with water (100 ml) and brine (50 ml)
  3. dry with materialthen dried (MgSO4)
  4. customEvaporation
  5. customgave a gum which
  6. customis chromatographed over silica gel (500 g)
  7. washeluting with 25-60% ethyl acetate-hexane

Sources & evidence

ORD record
ord-5e3d206d4fb54c97ae03048e94cbcb38
Source dataset
uspto-grants-2002_05
Patent number
US06387896B1

Reaction notes

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