Methanesulfonyl chloride → HCID 57038968, compound

HRID 414070Notes

Reaction equation

HRID 414070 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C@@H:5]1[O:10][C:9]2[CH:11]=[C:12]3[C:17](=[CH:18][C:8]=2[NH:7][C:6]1=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13]3.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>ClCCl.C(N(CC)CC)C>[S:21]([O:1][CH2:2][CH2:3][CH2:4][C@@H:5]1[O:10][C:9]2[CH:11]=[C:12]3[C:17](=[CH:18][C:8]=2[NH:7][C:6]1=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13]3)([CH3:20])(=[O:23])=[O:22]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 14304678HCID 14304678, compound

Product 1

HCID 57038968HCID 57038968, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred , ice-cooled suspension of (S)-6,7,8,9-tetrahydro-2-(3-hydroxypropyl)-2H-naphtho[2,3-b][1,4] oxazin-3(4H)-one (1.15 g) in a mixture of dichloromethane (40 ml) and triethylamine (0.45 g), was added dropwise methanesulfonyl chloride (1.01 g). The whole was stirred at 0° C. for 1.5 hour, washed with water and dried over magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography on silica gel (60 g) with ethyl acetate-hexane (3:2, v/v). The resulting crystals were recrystallized from methanol to yield (S)-6,7,8,9-tetrahydro-2-(3-mesyloxypropyl)-2H-naphto[2,3-b][1,4]oxazin-3(4H)-one as colorless needles (1.19 g, 79.7%), m.p. 153°-154° C. [α]D26 +4.8° (c=0.8, CHCl3).

Workup

  1. temperatureTo a stirred , ice-cooled
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by column chromatography on silica gel (60 g) with ethyl acetate-hexane (3:2
  6. customThe resulting crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-0d392cfddccd4b15918c89b999d8046f
Source dataset
uspto-grants-1988_12
Patent number
US04789675

Reaction notes

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