Hydrochloric Acid → HCID 69512874, compound

HRID 1182287Notes

Reaction equation

HRID 1182287 reaction equation
[OH:1][CH:2]([C@@H:14]([NH:19]C(=O)OC(C)(C)C)[CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)(=[O:7])=[O:6].O[C@@H]([C@@H](NC(=O)OC(C)(C)C)CCCC)CNS(C1C=CC=CN=1)(=O)=O.[ClH:53]>O1CCOCC1>[ClH:53].[NH2:19][C@@H:14]([CH2:15][CH2:16][CH2:17][CH3:18])[C@@H:2]([OH:1])[CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 58981686HCID 58981686, compoundHCID 86596687HCID 86596687, compound

Product 1

HCID 69512874HCID 69512874, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 5.0 g (13 mmol) of tert-butyl (1S)-1-{(1SR)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate & tert-butyl (1S)-1-{(1R)-1-hydroxy-2-[(2-pyridinylsulfonyl)amino]ethyl}pentylcarbamate in 15 mL of dioxane was added 20 mL of 4M hydrochloric acid in dioxane. The reaction mixture was stirred for 2 h and concentrated under reduced pressure to leave 4.2 g (>99) of N-[(2S,3S)-3-amino-2-hydroxyheptyl]-2-pyridinesulfonamide hydrochloride & N-[(2R,3S)-3-amino-2-hydroxyheptyl]-2-pyridinesulfonamide hydrochloride. 1H-NMR (400 MHz, DMSO-d6): δ 8.71 (s, 1H), 8.10–7.92 (m, 5H), 7.79–7.65 (m, 2H), 3.86 (s, 1H), 3.16-2.91 (m 3H), 1.58–1.33 (m, 2H), 1.20 (m, 4H), 0.84 (m, 3H); ES-LCMS m/z 288 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c4379a1973fb49d0ab6de5ccd40e9b34
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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