Thionyl Chloride → 83552-28-7

HRID 1463033Notes

Reaction equation

HRID 1463033 reaction equation
Cl.C[C@H]1CN[C@H]([C:8](O)=[S:9])C1.S(Cl)([Cl:13])=[O:12].Cl.C[N:17]1[CH2:25][CH2:24][CH2:23][C@H:18]1[C:19]([O:21][CH3:22])=S>CO>[ClH:13].[CH3:8][S:9][C@H:24]1[CH2:25][NH:17][C@H:18]([C:19]([O:21][CH3:22])=[O:12])[CH2:23]1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 131713602HCID 131713602, compoundHCID 178461574HCID 178461574, compound

Product 1

HCID 1403622683552-28-7

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of (trans)-4- methylthio-L-proline, hydrochloride (1.5 g., 7.59 mmole) [Patchett et al., "Studies on Hydroxyproline", JACS, Vol. 79, p. 185-192 (1957)] in 40 ml. of methanol at -30° under argon is added 3.32 ml. (6 eq.) of thionyl chloride dropwise over 5 minutes. The reaction mixture is worked up according to the procedure of Example 95(e). Recrystallization from acetonitrile/ether gives 630 mg. of (trans)-4- (methylthio-L-proline, methyl ester, hydrochloride as a colorless, crystalline material; m.p. 155-156°; [α]D20 =-11.3° (c=1.71, methanol).

Workup

  1. customRecrystallization from acetonitrile/ether
  2. customgives 630 mg

Sources & evidence

ORD record
ord-dbd3531bd35b4d3fb1a8f5b118302921
Source dataset
uspto-grants-1984_07
Patent number
US04462943

Reaction notes

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