1,2-Dichloroethane → HCID 54288719, compound

HRID 1902161Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:8]2([CH2:13][CH2:12][N:11]([C:14](=[O:33])[CH:15]([NH:25]C(OC(C)(C)C)=O)[CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:10][CH2:9]2)[CH2:7]1)=[O:5])[CH3:2].C(O)(C(F)(F)F)=O.[C:47]([NH:54][C:55]([CH3:60])([C:57](O)=[O:58])[CH3:56])([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>>[CH2:1]([O:3][C:4]([CH:6]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:8]2([CH2:13][CH2:12][N:11]([C:14](=[O:33])[CH:15]([NH:25][C:57](=[O:58])[C:55]([NH:54][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])([CH3:60])[CH3:56])[CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:10][CH2:9]2)[CH2:7]1)=[O:5])[CH3:2]

Participants

Reactant 6

HCID 111,2-Dichloroethane

HCID 6422Trifluoroacetic acid

HCID 79724-Methylmorpholine

HCID 757711-Hydroxybenzotriazole

HCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine

HCID 70344672HCID 70344672, compound

Product 1

HCID 54288719HCID 54288719, compoundYield 62.1%

Procedure

The title compound from Step A (155 mg, 0.29 mmol) was treated with TFA as in Step A and the residue was reacted with BOC-α-methyl alanine (73.5 mg, 0.377 mmol), EDC (72.0 mg, 0.377 mmol), HOBT (53 mg, 0.377 mmol), NMM (0.032 ml, 0.290 mmol) according to the procedure used for Example 1, Step A. Flash chromatography provided the title compound (112 mg, 0.18 mmol).

Sources & evidence

ORD record: ord-199e300a68124a479c0ab98001482805
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05578593

Reaction notes

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