(R)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonate → (S)-Methanesulphonic acid 2-Boc-aminopropyl ester

HRID 1852532Notes

Reaction equation

HRID 1852532 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:16])[CH2:10][O:11][S:12]([CH3:15])(=[O:14])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([C@@](N)(C)CO)(OC(C)(C)C)=O>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:16])[CH2:10][O:11][S:12]([CH3:15])(=[O:14])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 14427185(R)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonateHCID 86619943HCID 86619943, compound

Product 1

HCID 10753379(S)-Methanesulphonic acid 2-Boc-aminopropyl esterYield 97%

Procedure

In the same manner was prepared methanesulfonic acid (R)-2-tert-butoxycarbonylamino-propyl ester (white solid) using the 2-(R)-boc-2-amino-propanol as starting material (yield=14.09 g, 97% yield); 1H NMR (400 MHz, CDCl3) δ ppm 4.55-4.67 (1 H, m), 4.17-4.27 (1 H, m), 4.11-4.17 (1 H, m), 3.90-4.02 (1 H, m), 3.02 (3 H, s), 1.43 (9 H, s), 1.22 (3 H, d, J=6.85 Hz).

Sources & evidence

ORD record
ord-4053e66e35e3473cb58d9e3d9c236c05
Source dataset
uspto-grants-2015_02
Patent number
US08962622B2

Reaction notes

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