Hydrochloric Acid → (3S)-3-amino-7-{[(dimethylamino)sulfonyl]amino}-2-hydroxy-N-(3-pyridinylmethyl)heptanamide dihydrochloride

HRID 1180757Notes

Reaction equation

HRID 1180757 reaction equation
[CH3:1][N:2]([CH3:32])[S:3]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][C@H:11]([NH:24]C(=O)OC(C)(C)C)[CH:12]([OH:23])[C:13](=[O:22])[NH:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)(=[O:5])=[O:4].[ClH:33]>C(OCC)(=O)C>[ClH:33].[ClH:33].[NH2:24][C@@H:11]([CH2:10][CH2:9][CH2:8][CH2:7][NH:6][S:3]([N:2]([CH3:32])[CH3:1])(=[O:5])=[O:4])[CH:12]([OH:23])[C:13]([NH:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58979667tert-butyl(1S)-5-{[(dimethylamino)sulfonyl]amino}-1-{1-hydroxy-2-oxo-2-[(3-pyridinylmethyl)amino]ethyl}pentylcarbamate

Product 1

HCID 69237893(3S)-3-amino-7-{[(dimethylamino)sulfonyl]amino}-2-hydroxy-N-(3-pyridinylmethyl)heptanamide dihydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 0° C. solution of 1.13 g (2.4 mmol) of tert-butyl (1S)-5-{[(dimethylamino)sulfonyl]amino}-1-{1-hydroxy-2-oxo-2-[(3-pyridinylmethyl)amino]ethyl}pentylcarbamate in 100 mL of ethyl acetate was bubbled with hydrogen chloride gas for 5 min and stirred at room temperature for 30 min before being concentrated under reduced pressure to afford 1.06 g (>99%) of (3S)-3-amino-7-{[(dimethylamino)sulfonyl]amino}-2-hydroxy-N-(3-pyridinylmethyl)heptanamide dihydrochloride. 1H NMR (300 MHz, DMSO-d6) δ 8.92 (t, J=6 Hz, 1H), 8.76 (m, 2H), 8.09 (bs, 1H), 7.87 (m, 2H), 7.17 (m, 1H), 6.68 (m, 1H), 4.46 (m, 2H), (4.32 (d, J=3 Hz) and 4.18 (d, J=3 Hz), 1H), 3.37 (m, 1H), 2.83 (m, 2H), 2.67 (s, 6H), 1.25-1.60 (m, 6H). ES-LCMS m/z 374 (M+H).

Workup

  1. concentrationbefore being concentrated under reduced pressure

Sources & evidence

ORD record
ord-91f7ec3f22a44f24b9a60812ac9eadd5
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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