benzyl(2-{[(2S)-4-{[(benzyloxy)carbonyl]amino}-2-({[(8S,11S,14S)-14-[(tert-butoxycarbonyl)amino]-11-{3-[(tert-butoxycarbonyl)amino]propyl}-5,17-dihydroxy-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]henicosa-1(20),2(21),3,5,16,18-hexaen-8-yl]carbonyl}amino)butanoyl]amino}ethyl)carbamate → HCID 70806728, compound

HRID 269662Notes

Reaction equation

HRID 269662 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][NH:13][C:14](=[O:76])[C@@H:15]([NH:29][C:30]([C@H:32]1[NH:50][C:49](=[O:51])[C@H:48]([CH2:52][CH2:53][CH2:54][NH:55][C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[NH:47][C:46](=[O:63])[C@@H:45]([NH:64][C:65]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[O:66])[CH2:44][C:43]2[CH:72]=[C:39]([CH:40]=[CH:41][C:42]=2[OH:73])[C:38]2=[CH:74][C:34](=[C:35]([OH:75])[CH:36]=[CH:37]2)[CH2:33]1)=[O:31])[CH2:16][CH2:17][NH:18]C(OCC1C=CC=CC=1)=O)C1C=CC=CC=1>[Pd].C(O)(=O)C.O.C(O)C>[C:59]([O:58][C:56](=[O:57])[NH:55][CH2:54][CH2:53][CH2:52][C@@H:48]1[NH:47][C:46](=[O:63])[C@@H:45]([NH:64][C:65]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[O:66])[CH2:44][C:43]2[CH:72]=[C:39]([CH:40]=[CH:41][C:42]=2[OH:73])[C:38]2=[CH:74][C:34](=[C:35]([OH:75])[CH:36]=[CH:37]2)[CH2:33][C@@H:32]([C:30]([NH:29][C@H:15]([C:14]([NH:13][CH2:12][CH2:11][NH2:10])=[O:76])[CH2:16][CH2:17][NH2:18])=[O:31])[NH:50][C:49]1=[O:51])([CH3:60])([CH3:61])[CH3:62]

Participants

4

Reactant 1

HCID 131727166benzyl(2-{[(2S)-4-{[(benzyloxy)carbonyl]amino}-2-({[(8S,11S,14S)-14-[(tert-butoxycarbonyl)amino]-11-{3-[(tert-butoxycarbonyl)amino]propyl}-5,17-dihydroxy-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]henicosa-1(20),2(21),3,5,16,18-hexaen-8-yl]carbonyl}amino)butanoyl]amino}ethyl)carbamate

Product 1

HCID 70806728HCID 70806728, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 86584229Acetic acid ethanol waterSolvent

Procedure

29 mg (0.027 mmol) of benzyl(2-{[(2S)-4-{[(benzyloxy)carbonyl]amino}-2-({[(8S,11S,14S)-14-[(tert-butoxycarbonyl)amino]-11-{3-[(tert-butoxycarbonyl)amino]propyl}-5,17-dihydroxy-10,13-dioxo-9,12-diazatricyclo[14.3.1.12,6]henicosa-1(20),2(21),3,5,16,18-hexaen-8-yl]carbonyl}amino)butanoyl]amino}ethyl)carbamate (Example 191A) are added into 8 ml of a 4:1:1 acetic acid/water/ethanol mixture. 2.5 mg of palladium on activated carbon (10%) are added thereto, and the mixture is then hydrogenated at RT under atmospheric pressure for 15 h. The reaction mixture is filtered through prewashed kieselguhr and washed with ethanol, and the filtrate is concentrated on a rotary evaporator in vacuo.

Workup

  1. filtrationThe reaction mixture is filtered through prewashed kieselguhr
  2. washwashed with ethanol
  3. concentrationthe filtrate is concentrated on a rotary evaporator in vacuo

Sources & evidence

ORD record
ord-1162fd1544f542bc9e81a2bab41e5ee2
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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