Hydrochloric Acid → HCID 178442412, compound

HRID 979388Notes

Reaction equation

HRID 979388 reaction equation
C([O:5][C:6]([CH2:8][O:9]/[N:10]=[C:11](/[C:46]1[N:47]=[C:48]([NH:51]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:49][CH:50]=1)\[C:12]([NH:14][C@@H:15]1[C:44](=[O:45])[N:17]2[C:18]([C:28]([O:30]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:29])=[C:19](/[CH:22]=[CH:23]\[C:24]#[C:25][CH2:26][CH3:27])[CH2:20][S:21][C@H:16]12)=[O:13])=[O:7])(C)(C)C.[ClH:71]>C(O)=O>[ClH:71].[NH2:51][C:48]1[S:49][CH:50]=[C:46](/[C:11](=[N:10]/[O:9][CH2:8][C:6]([OH:7])=[O:5])/[C:12]([NH:14][C@@H:15]2[C:44](=[O:45])[N:17]3[C:18]([C:28]([OH:30])=[O:29])=[C:19](/[CH:22]=[CH:23]\[C:24]#[C:25][CH2:26][CH3:27])[CH2:20][S:21][C@H:16]23)=[O:13])[N:47]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 172938855HCID 172938855, compound

Product 1

HCID 178442412HCID 178442412, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A stirred solution of the product of stage (d) in formic acid (0.8 ml) was treated with 11M hydrochloric acid (56 μl). After 2.5 h the reaction mixture was filtered and the filtrate was added dropwise to vigorously stirred ether (50 ml). The precipitated solid was collected by filtration, washed with ether and dried in vacuo to give the title compound as a solid (78 mg); νmax (Nujol) 3280 (--NH), 2200 (C≡C), 1776 (β-lactam); τ(DMSO-d6) values include 0.27 (NH), 3.24 (--CH=CH--C≡C), 4.24 (--CH=CH--C≡C), 4.17 (7H), 4.72 (6H), 5.28 (OCH2CO2H), 7.68 (C≡C--CH2) and 8.86 (C≡C--CH2CH3).

Workup

  1. filtrationAfter 2.5 h the reaction mixture was filtered
  2. additionthe filtrate was added dropwise to vigorously stirred ether (50 ml)
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-4ea021d552014d8d959cd2999c9bfd24
Source dataset
uspto-grants-1987_05
Patent number
US04666899

Reaction notes

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