Hydrochloric Acid → HCID 131717953, compound

HRID 1586697Notes

Reaction equation

HRID 1586697 reaction equation
[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.CN1CCOCC1.C(OC(Cl)=O)C(C)C.Cl.[NH2:32][C@H:33]([C:45]([N:47]1[CH2:65][CH2:64][CH2:63][C@H:48]1[C:49]([NH:51][C@H:52]([C:60]([NH2:62])=[O:61])[CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:50])=[O:46])[CH2:34][C:35](=[O:44])[O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(OCC)(=O)C.CC(N(C)C)=O>[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([NH:32][C@H:33]([C:45]([N:47]1[CH2:65][CH2:64][CH2:63][C@H:48]1[C:49]([NH:51][C@H:52]([C:60]([NH2:62])=[O:61])[CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:50])=[O:46])[CH2:34][C:35](=[O:44])[O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:5]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 131717954HCID 131717954, compound

Product 1

HCID 131717953HCID 131717953, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

The mixed anhydride prepared from Boc-Pro (3.44 g, 16 mmoles), N-methyl morpholine (1.76 mL, 16 mmoles) and isobutylchloroformate (2.08 mL, 16 mmoles) in ethyl acetate (160 mL) was treated with the solution of HCl.Asp(OBzl)-Pro-Phe-NH2 and N-methyl morpholine (1.76 mL, 16 mmoles) in dimethylacetamide (30 mL). The reaction conditions and the product work up were described earlier. The product was crystallized from ethyl acetate-hexane.

Workup

  1. customThe reaction conditions
  2. customThe product was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-641475a280184d00809fd75c17ad45be
Source dataset
uspto-grants-1993_06
Patent number
US05215964

Reaction notes

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