Diisopropylethylamine → HCID 178523914, compound

HRID 366056Notes

Reaction equation

HRID 366056 reaction equation
[C:1]1([CH:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:8]([NH:10][C@H:11]([C:16]([NH:18][C@H:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20][OH:21])=[O:17])[CH2:12][CH2:13][CH2:14][NH2:15])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:34]([NH:44][C:45](=[N:48][C:49]([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:50])SC)([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35].CCN(C(C)C)C(C)C>CN(C=O)C>[C:49]([NH:48][C:45](=[N:44][C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])[NH:15][CH2:14][CH2:13][CH2:12][C@@H:11]([C:16]([NH:18][C@H:19]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:20][OH:21])=[O:17])[NH:10][C:8](=[O:9])[CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([O:51][CH2:52][C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)=[O:50]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 46642131,3-Bis(benzyloxycarbonyl)-2-methylisothioureaHCID 86755915(R)-N2-(Diphenylacetyl)-(S)-N-(2-hydroxy-1-phenylethyl)ornithine amide

Product 1

HCID 178523914HCID 178523914, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to the method described in Example 4(f) above from (R)-N2 -(diphenylacetyl)-(S)-N-(2-hydroxy-1-phenylethyl)ornithine amide (0.5 g; 1.12 mmol; from step (d) above), N,N'-bis(Cbz)-S-methyl-isothiourea (0.603 g; 1.68 mmol), DiPEA (0.2 mL) and DMF (15 mL), yielding 0.386 g of the sub-title compound.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-daa69e25f4d44639b7f50f3f5e8d67e2
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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