Triethylamine → HCID 178490624, compound

HRID 366072Notes

Reaction equation

HRID 366072 reaction equation
Cl.[C:2]1([CH:8]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:9]([NH:11][C@@H:12]([C:17]([NH:19][C@H:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[CH2:21][OH:22])=[O:18])[CH2:13][CH2:14][CH2:15][NH2:16])=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:37]([NH:47][C:48](=[N:51][C:52]([O:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)=[O:53])SC)([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38].C(N(CC)CC)C.CCN(C(C)C)C(C)C>CN(C)C=O>[C:52]([NH:51][C:48](=[N:47][C:37]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38])[NH:16][CH2:15][CH2:14][CH2:13][C@@H:12]([C:17]([NH:19][C@H:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[CH2:21][OH:22])=[O:18])[NH:11][C:9](=[O:10])[CH:8]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([O:54][CH2:55][C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1)=[O:53]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81531DiisopropylethylamineHCID 46642131,3-Bis(benzyloxycarbonyl)-2-methylisothioureaHCID 131722079(R)-N2-(Diphenylacetyl)-(R)-N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]-ornithine amide hydrochloride

Product 1

HCID 178490624HCID 178490624, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to the method described in Example 4(f) above from (R)-N2 -(diphenylacetyl)-(R)-N-[2-hydroxy-1-(4-methoxyphenyl) ethyl]ornithine amide hydrochloride (0.57 g; 1.11 mmol; from step (d) above), N,N'-bis(Cbz)-S-methylisothiourea (0.44 g; 1.22 mmol), triethylamine (0.17 g; 1.67 mmol; instead of DiPEA) and dimethyl formamide (10 mL), 60 hours reaction time. Concentration under vacuum gave the crude product which was chromatographed on silica eluting with CH2Cl2 :EtOAc (3:1), then CH2Cl2 :EtOAc (1:1), to give pure sub-title compound as a solid (0.48 g).

Workup

  1. customPrepared
  2. concentrationConcentration under vacuum
  3. customgave the crude product which
  4. customwas chromatographed on silica eluting with CH2Cl2 :EtOAc (3:1)

Sources & evidence

ORD record
ord-c80b30a89fe749b6bc9e78fa173b7976
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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