HCID 131710172, compound → HCID 131710173, compound

HRID 1606834Notes

Reaction equation

HRID 1606834 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:7]([NH:9][CH2:10][C:11]([NH:13][C@H:14]([C:16]([NH:18][C@H:19]([C:29]([NH:31][C@H:32]([C:41]([NH:43][C@H:44]([C:54]([NH:56][C@H:57]([C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])[CH2:58][O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:55])[CH2:45][CH2:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:42])[CH2:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:30])[CH2:20][CH2:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:17])[CH3:15])=[O:12])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5]>C(O)C>[NH2:1][C@H:2]([C:7]([NH:9][CH2:10][C:11]([NH:13][C@H:14]([C:16]([NH:18][C@H:19]([C:29]([NH:31][C@H:32]([C:41]([NH:43][C@H:44]([C:54]([NH:56][C@H:57]([C:64]([O:66][C:67]([CH3:68])([CH3:70])[CH3:69])=[O:65])[CH2:58][O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:55])[CH2:45][CH2:46][C:47](=[O:53])[O:48][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:42])[CH2:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:30])[CH2:20][CH2:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:17])[CH3:15])=[O:12])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5]

Participants

3

Reactant 1

HCID 131710172HCID 131710172, compound

Product 1

HCID 131710173HCID 131710173, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.47 g. (5.7 mmoles) of Z-25-31-OtBu are dissolved in a mixture of 220 ml. of ethanol and 20 ml. of DMF, and gaseous hydrogen is bubbled into the mixture for 1 hour in the presence of 1 g. of palladium-on-carbon. The catalyst is removed by filtration, the filtrate is evaporated to dryness, and the gelly residue is triturated with ether. The solid is filtered off and washed. 4.9 g. (86.2 %) of H-25-31 -OtBu are obtained. M.p.: 174°-176° C (under decomposition, Rf3 = 0.2.

Workup

  1. customof DMF, and gaseous hydrogen is bubbled into the mixture for 1 hour in the presence of 1 g
  2. customThe catalyst is removed by filtration
  3. customthe filtrate is evaporated to dryness
  4. customthe gelly residue is triturated with ether
  5. filtrationThe solid is filtered off
  6. washwashed
  7. custom(86.2 %) of H-25-31 -OtBu are obtained

Sources & evidence

ORD record
ord-712da2291e944520a0f9f0043392b8f4
Source dataset
uspto-grants-1976_04
Patent number
US03953415

Reaction notes

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