Methanesulfonyl chloride → HCID 21701942, compound

HRID 1596444Notes

Reaction equation

HRID 1596444 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:33]=[CH:32][C:10]([O:11][CH2:12][CH:13]([OH:31])[CH2:14][N:15]2[CH2:22][CH:21]3[CH2:23][CH:17]([CH2:18][N:19]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20]3)[CH2:16]2)=[CH:9][CH:8]=1>N1C=CC=CC=1>[OH:31][CH:13]([CH2:12][O:11][C:10]1[CH:32]=[CH:33][C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:8][CH:9]=1)[CH2:14][N:15]1[CH2:22][CH:21]2[CH2:23][CH:17]([CH2:18][N:19]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:20]2)[CH2:16]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 57262422HCID 57262422, compound

Product 1

HCID 21701942HCID 21701942, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

MsCl (0.50 g; 4.40 mmol) was added to a stirred solution of tert-butyl 7-[3-(4-aminophenoxy)-2-hydroxypropyl]-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (1.68 g; 4.29 mmol; see Example 13 above) in pyridine (20 mL). The reaction mixture was stirred for 2.5 h and subsequently concentrated. The residue was partitioned between DCM and NaHCO3 (sat.), the organic layer separated, dried and concentrated. Purification using column chromatography (gradient 0 to 10% MeOH in DCM) gave the title compound in a 87% yield. 13C NMR (CDCl3): δ 28.70, 28.70, 28.84, 29.09, 29.42, 31.93, 38.77, 47.64, 49.42, 57.01, 60.29, 61.84, 65.20, 70.79, 79.50, 115.48, 116.32, 124.53, 129.40, 155.94, 157.28.

Workup

  1. concentrationsubsequently concentrated
  2. customThe residue was partitioned between DCM and NaHCO3 (sat.)
  3. customthe organic layer separated
  4. customdried
  5. concentrationconcentrated
  6. customPurification

Sources & evidence

ORD record
ord-f81773ec6c0e435a9deeaf0369baa6dd
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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