Water → HCID 59547332, compound

HRID 2038572Notes

Reaction equation

HRID 2038572 reaction equation
[NH2:1][CH2:2][C:3]1([CH2:22][C:23]([O:25]CC)=[O:24])[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:5]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:4]1.[OH-].[Li+].O>C1COCC1>[NH2:1][CH2:2][C:3]1([CH2:22][C:23]([OH:25])=[O:24])[CH2:4][C@@H:5]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[N:6]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 59547304HCID 59547304, compound

Product 1

HCID 59547332HCID 59547332, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ester (2S)-di-tert-butyl 4-(aminomethyl)-4-(2-ethoxy-2-oxoethyl)pyrrolidine-1,2-dicarboxylate (C6) (560 mg, 1.45 mmol) was dissolved in THF (12 ml). To this was added 1N lithium hydroxide in water (2.9 ml, 2.9 mmol, 2.0 eq). The mixture was stirred at room temperature overnight. The reaction was cooled to 0° C. and quenched with 1N hydrochloric acid in water. The mixture was blown to dryness with N2 gas and stripped from acetonitrile several times to give 2-((5S)-3-(aminomethyl)-1,5-bis(tert-butoxycarbonyl)pyrrolidin-3-yl)acetic acid (D6) (1.45 mmol) as a glassy solid. 1H NMR (DMSO) δ 1.35 (m, 18H), 2.00 (m, 2H), 2.35 (m, 2H), 2.80 (m, 1H), 3.65 (m, 1H), 4.00 (m, 1H); LCMS for C17H30N2O6 358.21 [M], found ES+ 359.21 [M+H]+ and ES− 357.21 [M−H]− at 1.8 minutes retention time, using 10-90% acetonitrile/water (with 0.1% formic acid buffer) gradient over 5 minutes.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with 1N hydrochloric acid in water

Sources & evidence

ORD record
ord-aeb1c09f7aa64a24b5703bb5a8e124ea
Source dataset
uspto-grants-2013_11
Patent number
US08575208B2

Reaction notes

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