Hydrochloric Acid → (S)-2-({(3S,8S)-3-[3-(3,4-dichloro-benzyloxy)-phenyl]-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl}-amino)-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl ester dihydrochloride

HRID 391986Notes

Reaction equation

HRID 391986 reaction equation
C(OC([N:8]1[C@H:17]([C:18](=[O:41])[NH:19][C@H:20]([C:37]([O:39][CH3:40])=[O:38])[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[C:30]=3[CH3:36])=[CH:24][CH:23]=2)[CH2:16][C:15]2[CH:14]=[C:13]3[O:42][CH2:43][C@H:44]([C:46]4[CH:51]=[CH:50][CH:49]=[C:48]([O:52][CH2:53][C:54]5[CH:59]=[CH:58][C:57]([Cl:60])=[C:56]([Cl:61])[CH:55]=5)[CH:47]=4)[O:45][C:12]3=[CH:11][C:10]=2[CH2:9]1)=O)(C)(C)C.[ClH:62]>C(Cl)Cl>[ClH:60].[ClH:62].[CH3:40][O:39][C:37](=[O:38])[C@@H:20]([NH:19][C:18]([C@@H:17]1[CH2:16][C:15]2[CH:14]=[C:13]3[O:42][CH2:43][C@H:44]([C:46]4[CH:51]=[CH:50][CH:49]=[C:48]([O:52][CH2:53][C:54]5[CH:59]=[CH:58][C:57]([Cl:60])=[C:56]([Cl:61])[CH:55]=5)[CH:47]=4)[O:45][C:12]3=[CH:11][C:10]=2[CH2:9][NH:8]1)=[O:41])[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][C:29]2[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[C:30]=2[CH3:36])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58327379(3S,8S)-3-[3-(3,4-Dichloro-benzyloxy)-phenyl]-8-{(S)-2-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-1-methoxycarbonyl-ethylcarbamoyl}-2,3,8,9-tetrahydro-6H-[1,4]dioxino[2,3-g]isoquinoline-7-carboxylic acid tert-butyl ester

Product 1

HCID 66719635(S)-2-({(3S,8S)-3-[3-(3,4-dichloro-benzyloxy)-phenyl]-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl}-amino)-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl ester dihydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(3S,8S)-3-[3-(3,4-Dichloro-benzyloxy)-phenyl]-8-{(S)-2-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-1-methoxycarbonyl-ethylcarbamoyl}-2,3,8,9-tetrahydro-6H-[1,4]dioxino[2,3-g]-isoquinoline-7-carboxylic acid tert-butyl ester (50 mg) was taken in 2 mL of DCM and cooled to 0° C., HCl (0.5 mL, 4N in dioxane) was added and stirred at room temperature for 2 hours. All volatiles were evaporated and residue was washed with hexanes and dried under vacuum to get (S)-2-({(3S,8S)-3-[3-(3,4-dichloro-benzyloxy)-phenyl]-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl}-amino)-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl ester dihydrochloride (46 mg).

Workup

  1. customAll volatiles were evaporated
  2. washresidue was washed with hexanes
  3. customdried under vacuum

Sources & evidence

ORD record
ord-f8d1a87b279243b99642305ae5f423ac
Source dataset
uspto-grants-2013_02
Patent number
US08383644B2

Reaction notes

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