Hydrochloric Acid → (8S,11S,14S)-14-Amino-N-{(4S)-4-amino-6-[(2-aminoethyl)amino]-6-oxohexyl}-11-(3-aminopropyl)-9-ethyl-5,17-dihydroxy-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]henicosa-1(20),2(21),3,5,16,18-hexaene-8-carboxamide tetrahydrochloride

HRID 269696Notes

Reaction equation

HRID 269696 reaction equation
[ClH:1].C(OC(=O)[NH:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[NH:30][C:29](=[O:31])[C@@H:28]([NH:32]C(OC(C)(C)C)=O)[CH2:27][C:26]2[CH:40]=[C:22]([CH:23]=[CH:24][C:25]=2[OH:41])[C:21]2=[CH:42][C:17](=[C:18]([OH:43])[CH:19]=[CH:20]2)[CH2:16][C@@H:15]([C:44]([NH:46][CH2:47][CH2:48][CH2:49][C@H:50]([NH2:58])[CH2:51][C:52]([NH:54][CH2:55][CH2:56][NH2:57])=[O:53])=[O:45])[N:14]([CH2:59][CH3:60])[C:13]1=[O:61])(C)(C)C>O1CCOCC1>[ClH:1].[ClH:1].[ClH:1].[ClH:1].[NH2:32][C@H:28]1[CH2:27][C:26]2[CH:40]=[C:22]([CH:23]=[CH:24][C:25]=2[OH:41])[C:21]2=[CH:42][C:17](=[C:18]([OH:43])[CH:19]=[CH:20]2)[CH2:16][C@@H:15]([C:44]([NH:46][CH2:47][CH2:48][CH2:49][C@H:50]([NH2:58])[CH2:51][C:52]([NH:54][CH2:55][CH2:56][NH2:57])=[O:53])=[O:45])[N:14]([CH2:59][CH3:60])[C:13](=[O:61])[C@H:12]([CH2:11][CH2:10][CH2:9][NH2:8])[NH:30][C:29]1=[O:31]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131727164tert-Butyl{3-[(8S,11S,14S)-8-[({(4S)-4-amino-6-[(2-aminoethyl)amino]-6-oxohexyl}amino)carbonyl]-14-[(tert-butoxycarbonyl)amino]-9-ethyl-5,17-dihydroxy-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]henicosa-1(20),2(21),3,5,16,18-hexaen-11-yl]propyl}carbamate

Product 1

HCID 50938582(8S,11S,14S)-14-Amino-N-{(4S)-4-amino-6-[(2-aminoethyl)amino]-6-oxohexyl}-11-(3-aminopropyl)-9-ethyl-5,17-dihydroxy-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]henicosa-1(20),2(21),3,5,16,18-hexaene-8-carboxamide tetrahydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

0.1 ml of 4M solution of hydrogen chloride in dioxane is added to a solution of 7.5 mg (0.009 mmol) of tert-butyl{3-[(8S,11S,14S)-8-[({(4S)-4-amino-6-[(2-aminoethyl)amino]-6-oxohexyl}amino)carbonyl]-14-[(tert-butoxycarbonyl)amino]-9-ethyl-5,17-dihydroxy-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]henicosa-1(20),2(21),3,5,16,18-hexaen-11-yl]propyl}carbamate (Example 204A) in 0.1 ml of dioxane at 0° C. After 2 h at RT, the reaction solution is concentrated in vacuo, coevaporated with dichloromethane several times and dried under high vacuum. The residue is mixed with diethyl ether and concentrated.

Workup

  1. concentrationthe reaction solution is concentrated in vacuo
  2. customdried under high vacuum
  3. additionThe residue is mixed with diethyl ether
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e3abd474807c4186aca1ead51ea00c64
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

Loading…