Ethyl chloroformate → HCID 178473526, compound

HRID 1450180Notes

Reaction equation

HRID 1450180 reaction equation
[Cl:1]C(OCC)=O.N(C(OC(C)(C)C)=O)[C@@H](C(O)=O)CC1CCCCC1.[CH2:26]([O:28][C:29]([NH:31][C@@H:32]([C:40]([N:42]1[CH2:59][CH2:58][CH2:57][C@H:43]1[C:44]([NH:46][C@H:47]([CH:55]=[O:56])[CH2:48][CH2:49][CH2:50][NH:51][C:52](=[NH:54])[NH2:53])=[O:45])=[O:41])[CH2:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)=[O:30])[CH3:27].Cl.O>>[CH2:26]([O:28][C:29]([NH:31][C@@H:32]([C:40]([N:42]1[CH2:59][CH2:58][CH2:57][C@H:43]1[C:44]([NH:46][C@H:47]([CH:55]=[O:56])[CH2:48][CH2:49][CH2:50][NH:51][C:52](=[NH:53])[NH2:54])=[O:45])=[O:41])[CH2:33][CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1)=[O:30])[CH3:27].[ClH:1]

Participants

4

Reactant 3

HCID 10928Ethyl chloroformateHCID 2755927(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-cyclohexylpropanoic acidHCID 178473527HCID 178473527, compound

Product 1

HCID 178473526HCID 178473526, compound

Procedure

By methods substantially equivalent to those described in Examples 1-A, 1-B, 7-A, 1-D, 1-H and 1-I, using ethyl chloroformate in place of MeSO2Cl and using Boc-D-Cha-OH in place of Boc-D-Phe-OH, 0.6 g of EtOCO-D-Cha-Pro-Arg-H.HCl hydrate was prepared. EtOCO-D-Cha-Pro-Arg-H.HCl was purified by RPHPLC (95/5 (A/B) ramp to 60/40 (A/B), 240 min).

Workup

  1. customwas prepared
  2. customEtOCO-D-Cha-Pro-Arg-H.HCl was purified by RPHPLC (95/5 (A/B) ramp to 60/40 (A/B), 240 min)

Sources & evidence

ORD record
ord-2c91ee64994c4ac7a5e7c54b0cb4d02e
Source dataset
uspto-grants-1997_02
Patent number
US05602101

Reaction notes

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