4-Methylmorpholine → HCID 22951552, compound

HRID 276734Notes

Reaction equation

HRID 276734 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[CH:8][N:7]([CH2:10][CH2:11][CH2:12][C@H:13]([NH:17][C:18](=[O:44])[C@H:19]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([CH3:43])[CH:38]=2)[NH:20][C:21](=[O:35])[CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]([OH:16])=O)[N:6]=1)=[O:4].C[N:46]1CCOCC1.ClC(OCC(C)C)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[CH:8][N:7]([CH2:10][CH2:11][CH2:12][C@H:13]([NH:17][C:18](=[O:44])[C@H:19]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([CH3:43])[CH:38]=2)[NH:20][C:21](=[O:35])[CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:14]([NH2:46])=[O:16])[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 22951553HCID 22951553, compound

Product 1

HCID 22951552HCID 22951552, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-[4-(3-methoxycarbonyl-1H-pyrazol-1-yl)-1(S)-carboxybutyl]-3-methyl-Nα-(2,2-diphenylacetyl)-L-phenylalaninamide (0.3 g, 0.5 mmol)) and N-methylmorpholine (0.17 mL, 1.5 mmol) in CH2Cl2 (50 mL) is cooled to −10° C., and isobutyl chloroformate (0.065 mL, 0.5 mmol) is added dropwise over 10 minutes. After stirring for 15 minutes, ammnonia gas is bubbled into the solution at a moderately vigorous rate for 15 minutes. The solution is then warmed to room temperature over 30 min. CH2Cl2 is evaporated, the residue is treated with water (30 mL). The suspension is adjusted to pH=7 with 1 N HCl, and filtered. The solid is washed with water (50 mL) and dried in vacuo to yield N-[4-(3-methoxycarbonyl-1H-pyrazol-1-yl)-1(S)-(aminocarbonyl)-butyl]-3-methyl-Nα-(2,2-diphenylacetyl)-L-phenylalaninamide.

Workup

  1. customammnonia gas is bubbled into the solution at a moderately vigorous rate for 15 minutes
  2. customCH2Cl2 is evaporated
  3. additionthe residue is treated with water (30 mL)
  4. filtrationfiltered
  5. washThe solid is washed with water (50 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-b82b97723e284092a96e0ba43b07b812
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

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