benzyl(2-{[(3S)-3-{[(benzyloxy)carbonyl]amino}-6-({[(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)hexanoyl]amino}ethyl)carbamate → HCID 70806691, compound

HRID 269661Notes

Reaction equation

HRID 269661 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][NH:13][C:14](=[O:78])[CH2:15][C@@H:16]([NH:67]C(OCC1C=CC=CC=1)=O)[CH2:17][CH2:18][CH2:19][NH:20][C:21]([C@H:23]1[NH:41][C:40](=[O:42])[C@H:39]([CH2:43][CH2:44][CH2:45][NH:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[NH:38][C:37](=[O:54])[C@@H:36]([NH:55][C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:35][C:34]2[CH:63]=[C:30]([CH:31]=[CH:32][C:33]=2[OH:64])[C:29]2=[CH:65][C:25](=[C:26]([OH:66])[CH:27]=[CH:28]2)[CH2:24]1)=[O:22])C1C=CC=CC=1>[Pd].C(O)(=O)C.O.C(O)C>[C:50]([O:49][C:47](=[O:48])[NH:46][CH2:45][CH2:44][CH2:43][C@@H:39]1[NH:38][C:37](=[O:54])[C@@H:36]([NH:55][C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:35][C:34]2[CH:63]=[C:30]([CH:31]=[CH:32][C:33]=2[OH:64])[C:29]2=[CH:65][C:25](=[C:26]([OH:66])[CH:27]=[CH:28]2)[CH2:24][C@@H:23]([C:21]([NH:20][CH2:19][CH2:18][CH2:17][C@H:16]([NH2:67])[CH2:15][C:14]([NH:13][CH2:12][CH2:11][NH2:10])=[O:78])=[O:22])[NH:41][C:40]1=[O:42])([CH3:51])([CH3:52])[CH3:53]

Participants

4

Reactant 1

HCID 131727165benzyl(2-{[(3S)-3-{[(benzyloxy)carbonyl]amino}-6-({[(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)hexanoyl]amino}ethyl)carbamate

Product 1

HCID 70806691HCID 70806691, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 86584229Acetic acid ethanol waterSolvent

Procedure

12 mg (0.011 mmol) of benzyl(2-{[(3S)-3-{[(benzyloxy)carbonyl]amino}-6-({[(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)hexanoyl]amino}ethyl)carbamate (Example 190A) are added into 3 ml of a 4:1:1 acetic acid/water/ethanol mixture. 1.5 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-7a3ab6b1c65a493bb4e75959289da004
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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