Hydrochloric Acid → 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

HRID 441897Notes

Reaction equation

HRID 441897 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[Li].OC1C=CC=CN=1.[C:17](=O)([O-:34])[O:18][C:19]1([C:30](C)(C)C)[C:24](Cl)=C(Cl)C(Cl)=C(Cl)[CH:20]1Cl.Cl>[OH-].[Na+].O.C(Cl)(Cl)Cl.CN(C)C=O>[C:19]([O:18][C:17]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:34])([CH3:30])([CH3:24])[CH3:20]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 145742L-ProlineHCID 3028194LithiumHCID 86733569HCID 86733569, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-Yield 79%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

11.5 g. of L-proline is dissolved in 4N sodium hydroxide, and 100 ml. of dimethylformamide, 50 ml. of chloroform, 10.1 g. of the lithium salt of 2-hydroxypyridine and 36.6 g. of t-butylpentachlorophenyl carbonate are added thereto. The solution is stirred at room temperature for three hours, after which 100 ml. of chloroform and 200 ml. of water are added. After shaking, the water layer is acidified to a pH of 2 with 1N hydrochloric acid, and extracted with 200 ml. of ethyl acetate. The product is worked up as previously described to give t-butyloxycarbonyl-L-proline in 79 percent yield, m.p. 137° C.

Workup

  1. stirringAfter shaking
  2. extractionextracted with 200 ml

Sources & evidence

ORD record
ord-a70eafa4d8fa4b0fb82cd39fc24f505e
Source dataset
uspto-grants-1977_08
Patent number
USRE029369

Reaction notes

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