Chloroform → HCID 131711185, compound

HRID 2419482Notes

Reaction equation

HRID 2419482 reaction equation
[NH2:1][C@H:2]([C:18]([OH:20])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].CCN(CC)CC.[NH:28]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C@H:29]([C:42](ON1C(=O)CCC1=O)=[O:43])[CH2:30][CH2:31][C:32](=[O:41])[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(Cl)(Cl)Cl>CN(C=O)C>[NH:28]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C@H:29]([C:42]([NH:1][C@H:2]([C:18]([OH:20])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])=[O:43])[CH2:30][CH2:31][C:32](=[O:41])[O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 1715626epsilon-(Benzyloxycarbonyl)-L-lysineHCID 13242221Boc-glu(obzl)-osu

Product 1

HCID 131711185HCID 131711185, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of H-Lys(Z)-OH (0.89 g, 3.18 mmol) in DMF (25 ml) was stirred with Et3N (0.5 ml) and Boc-Glu(OBzl)-OSu (1.58 g, 3.5 mmol) at 0° C for 1 hr and 25° C for 24 hr. The reaction mixture was worked up as described above in Example 2 to produce a clear oil which was crystallized from EtOAc and petroleum ether to yield 1.47 g (77.4%); mp 110°-112° C.; [α]D25 +6.0° (c 1, CHCl3). Anal. Calcd for C31H41N3O9 (599.69): C, 62.08; H, 6.89; N, 7.00. Found: C, 62.04; H, 6.96; N, 7.10.

Workup

  1. customto produce a clear oil which
  2. customwas crystallized from EtOAc and petroleum ether
  3. customto yield 1.47 g (77.4%)

Sources & evidence

ORD record
ord-74e2e3d6b50e42ee94e1f70581d5d2de
Source dataset
uspto-grants-1978_08
Patent number
US04105652

Reaction notes

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