Methanol → methyl (2S,4R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylate sulphate

HRID 70109Notes

Reaction equation

[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]3[CH2:23][N:22](C(OC(C)(C)C)=O)[C@H:21]([C:31]([O-:33])=[O:32])[CH2:20]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[S:34](=[O:38])(=[O:37])([OH:36])[OH:35].[CH3:39]O>>[S:34]([OH:38])([OH:37])(=[O:36])=[O:35].[CH:5]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]3[CH2:23][NH:22][C@H:21]([C:31]([O:33][CH3:39])=[O:32])[CH2:20]3)=[O:17])[C:11]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:1]=2[CH:2]=[CH:3][CH:4]=1

Participants

Reactant 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 258060671,2-Pyrrolidinedicarboxylic acid, 4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, 1-(1,1-dimethylethyl) ester, (2S,4R)-

Product 1

HCID 66736107methyl (2S,4R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylate sulphate

Procedure

850 mg 1-tert.butyl (2S,4R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-1,2-dicarboxylate and 60 μl sulphuric acid are placed in 12 ml abs. methanol. The reaction mixture is then refluxed for 48 hours with stirring and then evaporated to dryness. 1.0 g product is obtained as a foam. Analytical HPLC-MS (method B): RT=1.80 min.

Workup

temperatureThe reaction mixture is then refluxed for 48 hours
customevaporated to dryness

Sources & evidence

ORD record: ord-4fec1999d3434021acfde3960142985c
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822474B2

Reaction notes

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