Hydrochloric Acid → Isobutyric acid (1s,2s)-6-fluoro-2-[2-({3-[(2-fluoro-ethyl)-(3-methoxy-2-methoxymethyl-2-methyl-propyl)-amino]-propyl}-methyl-amino)-ethyl]-1-isopropyl-1,2,3,4-tetrahydro-naphthalen-2-yl ester dihydrochloride salt

HRID 2090574Notes

Reaction equation

HRID 2090574 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C@H:8]([CH:12]([CH3:14])[CH3:13])[C@@:7]([O:35][C:36](=[O:40])[CH:37]([CH3:39])[CH3:38])([CH2:15][CH2:16][N:17]([CH2:19][CH2:20][CH2:21][N:22]([CH2:32][CH2:33][F:34])[CH2:23][C:24]([CH2:29][O:30][CH3:31])([CH3:28])[CH2:25][O:26][CH3:27])[CH3:18])[CH2:6][CH2:5]2.[ClH:41]>CCOC(C)=O>[ClH:41].[ClH:41].[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C@H:8]([CH:12]([CH3:14])[CH3:13])[C@@:7]([O:35][C:36](=[O:40])[CH:37]([CH3:39])[CH3:38])([CH2:15][CH2:16][N:17]([CH2:19][CH2:20][CH2:21][N:22]([CH2:32][CH2:33][F:34])[CH2:23][C:24]([CH2:29][O:30][CH3:31])([CH3:28])[CH2:25][O:26][CH3:27])[CH3:18])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 45381136isobutyric acid (1S,2S)-6-fluoro-2-[2-({3-[(2-fluoro-ethyl)-(3-methoxy-2-methoxymethyl-2-methyl-propyl)-amino]-propyl}-methyl-amino)-ethyl]-1-isopropyl-1,2,3,4-tetrahydro-naphthalen-2-yl ester

Product 1

HCID 86657122Isobutyric acid (1s,2s)-6-fluoro-2-[2-({3-[(2-fluoro-ethyl)-(3-methoxy-2-methoxymethyl-2-methyl-propyl)-amino]-propyl}-methyl-amino)-ethyl]-1-isopropyl-1,2,3,4-tetrahydro-naphthalen-2-yl ester dihydrochloride salt

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

411 mg of isobutyric acid (1S,2S)-6-fluoro-2-[2-({3-[(2-fluoro-ethyl)-(3-methoxy-2-methoxymethyl-2-methyl-propyl)-amino]-propyl}-methyl-amino)-ethyl]-1-isopropyl-1,2,3,4-tetrahydro-naphthalen-2-yl ester were dissolved in 10 mL EtOAc, the solution was cooled with an ice bath and 2.4 mL of 3M HCl in EtOAC were added. The reaction mixture was evaporated to dryness without heating to give the desired isobutyric acid (1S,2S)-6-fluoro-2-[2-({3-[(2-fluoro-ethyl)-(3-methoxy-2-methoxymethyl-2-methyl-propyl)-amino]-propyl}-methyl-amino)-ethyl]-1-isopropyl-1,2,3,4-tetrahydro-naphthalen-2-yl ester dihydrochloride salt.

Workup

  1. temperaturethe solution was cooled with an ice bath
  2. customThe reaction mixture was evaporated to dryness
  3. temperaturewithout heating

Sources & evidence

ORD record
ord-8d691f5156da42f4949101d52fe5495e
Source dataset
uspto-grants-2013_05
Patent number
US08436205B2

Reaction notes

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